Theoritical n,n dialkylation of tryptamines mechanism

[Xtal]

Hello everybody. This forum here looks like an interesting place with open minded people who won't scream "omg look at this stupid drug cook" or "f*cking meth junkie" when someone even mentions something remotely close to organic chemistry. So, with the hope that I will finally find some respectful, enlightening information, I give the following anecdote:

My friend found some really interesting shit the other day about this obscure high yielding reductive amination of primary amines with aldehydes or ketones to produce a tertiary amine using sodium borohydride. The ref is given as B. L. Sondengam, Tet. Lett. 3, 261 (1973), my friend has really not seen this rxn around in any other literature or discussion so he assumes its still novel and experimental. Here it is (found on the rhodium site for Tryptamine to [You know what chemical].)

"Formalin (35%, 35 mmol) was added with stirring to a solution of holafébrine (primary amine) 3 mmol in methanol (10 ml) and the solution was refluxed for 30 min. After cooling, 400 mg NaBH4 was added slowly. After 1 h the reaction was evaporated and the mixture was extracted with CH2Cl2. Evaporation yields 85% iréhine (dimethyl-holafébrine)."

Here's what the author who referenced this pathway had to say about it.

"These one-pot reactions utilize only cheap and (more or less) non-toxic chemicals (no carcinogenic and expensive methyl iodide!). Because of the aprotic, non acidic reaction and work-up conditions no cyclization to β-carbolines should occur. The yields after purification are good to excellent (phenylethylamine: 72%, diisopropylamine: 92%, holafébrine: 85%)."

So my friend bought what the guy was selling and thinks that this method is more economical than a similar cyanoborohydride reduction.

Does anybody have any thoughts on the feasibility of this pathway in alkylating tryptamines? Where does the H2O go when it is released from the Hemiaminal? Because removal of H2O is what drives the reductive amination rxn forward. My friend has heard good things about MDP2P reduction aminations with NaBH4, with yields of >90%(!) so my friend is naturally quite hopeful this pathway will do the same justice. Any feed back is appreciated. Thanks.

[Xtal]

Seeing bunghole's previous thread on n,n alkylation, this method in my opinion, if feasible, is superior. Hunig's base is expensive. Alkyl halides are dangerous and expensive. Besides, I have a feeling that SN2 substitutions aren't the best yielding anyway. A reductive amination would be simpler and drastically higher yielding, starting from freebase tryptamine (actually relatively cheap).

P.S. viva la totse

[idontlie]

Sodium Borohydride reacts with water making it a "nonissue" w/ excess?

[Xtal]

Hmm quite interesting, thanks for the thoughtful input. It does say that NaBH4 reacts quite vigorously w/ H2O. Upon further searching, I found that NaBH4 reacts with water to produce H2. Any idea what the other products are?.

It said in the MDMA reductive amination pathway that the NaBH4 actually doesn't reduce the methanol solvent all the way down to formaldehyde cuz the primary amine (methylamine) is more reactive ie a better nucleophile. And speaking of which, I suppose the reason why SN2 substitutions with primary amines (tryptamines) and an alkyl halide yields so low is because the primary amine is not a very good nucleophile, ie not as strong of a base (the wikipedia Sn2 article says: "stronger bases are better nucleophiles", thus the amine would have trouble muscling the bromine out of its spot.

The same situation is evident in the SN2 substitution of bromosafrole w/ for example Ammonia, which is a so-so nucleophile, as compared to methylamine, which is a stronger base, hence better nucleophile... which hypothetically would mean better yields when being cooked in the bomb. ref:H. Huson (aka Strike), Total Synthesis II 157 (1999).

So all you cooks out there take delight... 3 theoretical pathways (reductive methylation of tryptamines, reductive amination of MDP2P, and SN2 of bromosafrole w/ methylamine) for the price of one. (http://www.erowid.org/archive/rhodiu...min.nabh4.html - the link for the MDP2P reduction w/ NaBH4)

[fcknut]

Reductive amination with sodium borohydride is a pretty standard procedure...

And the reason yields of amine alkylation with alkyl halides tends to be low, is more to do with formation of quaternary salts, IIRC...

[Xtal]

Yeah... the Hunig's base is used to get rid of the quat in a halide alkylation, but whatevers haha it will be a long while before my friend even has the necessary funds to start his little science experiment. Thanks everybody for their thoughtful feedback.

Edit: Upon further reading, I have discovered that this process has been referenced before in this very forum, under the thread Tryptophan Decarboxylation... I suppose anyone wouldn't have actually done the procedure? If so, how were the yields?

[Hydroponichronic]

Originally Posted by idontlie

Sodium Borohydride reacts with water making it a "nonissue" w/ excess?

NaBH₄ reacts with acidic water. Otherwise it'll stick around for a bit. Also, excess might react with the alkene at the 2 position, but I might be wrong.

The biggest thing, here, is that you can't exactly buy NaBH₄ at Walgreens, now can you? If you could source the stuff, you could reductively aminate to you heart's content, but chances are, you can't.

[stateofhack]

Works fine with triacetoxyborohydride, which is a joke to prepare (assuming you have NaBH4). Its pretty expensive stuff to buy otherwise

Also you WILL have to do a column to get your final product out and clean (DCM with MeOH gradient of 5 to 10% and a 4 drops of 5M ammonia in methanol).

Good luck.

[BungHole]

Well, I know someone with personal experience that has proven Hunig's base isn't totally necessary for alkylation with haloalkanes, and that it currently is the most OTC and easiest method. But yields aren't great, and alkyl halides are still very, very nasty, so.... on topic....

The elves of Mt. Kilimanjaro have recently been focusing on reductive alkylation/amination, especially for MIPT. They never thought a borohydride would be practica(because they can't get it, although they're trying to figure out how to make it, or atleast get it for hydrogen fuel cells), so they didn't even think far enough into it to realize it doesn't work (thanks for the bad news Ford ). But what Hydro has been thinking is Zn/HCl, and what the elves have been thinking is Urushibara nickel catalyst(yes, yes, I know, the elves want cancer for sure ). Although zinc powder is easily acquired, they haven't heard good things about yields from this, unlike nickel catalysts. So theoretically, a little HCl, some American currency, and some aluminum foil could go a long way....

So what they have been thinking of is a little hybridization. They prefer biological sources of the dimethyl analogues, so they say fuck the reductive amination of formaldehyde, and they already have ethyl bromide begging to be gotten rid of, an don't feel like obtaining acetaldehyde just yet (although it sounds like there are two very easy methods in oxidation over copper catalyst and oxidation with H2O2 and catalyst, ethanol being the substrate of course). Of course, there is also the obvious and probably ridiculously easy reductive amination of acetone, but DIPT is sort of on the back burner for them. They have a bigger interest. MIPT. Now, they have no source of formaldehyde currently, but it's easy enough to make. But really, they don't want to do it this way for some reason, it just doesn't seem as interesting. As interesting as hybridizing this bitch.

So this is the plan: Although Methyl iodide is nasty, it's still easy enough to make and handle with care(skin/membrane protection, ventilation, cold temperature), and they prefer small scale anyway. So what's a little methyl iodide?(read: what's a little cancer? Yes, they have a death wish.) Really, alkylation with alkyl halides can be efficient, if one doesn't have to be worried about over alkylation to the quaternary salt. Which you really don't with monoalkylation. So, a monomethylation with methyl iodide really isn't too bad of an idea, if you aren't choosing to just stop there. One mole tryptamine plus one mole methyl iodide, no base, and you got a decent yield of monomethyltryptamine. And God, do they want to reductively aminate some acetone and destroy some $0.05 coin pieces at the same time. They sure as hell have the tryptamine, that's for sure. So I think you see where I'm going with this....

Spoiler: Click to toggle

Originally Posted by BungHole

Okay, the elves that live under the mountain near my hut have devised a plan.

You see, the elves, they has tryptophan, and wants the MIPT, you know, for mind expansion and stimulation and what not. This "tryptophan" was proven to be a "relatively pure amino acid" by dissolving in "baking soda solution." So hopefully the "tryptophan" is tryptophan.

Okay, so herez teh plan:

Teh tripp d'amine

• 200 ml of "paint removal grade" distillate of pine tree will be placed in a 500 ml RB flask.

• 20 g of " 100% pure, FDA approved tryptophan" will be added.

• 30 ml of distillate of pine tree containing ~ 1 ml of Care away essential oil (made by steam distilling approximately 170 g of seeds of the caraway plant and extracting distillate with turps).

• A condenser will be placed atop the flask, and a balloon/lamb skin condom will go over the top.

• This will be heated/refluxed for six hours or until mixture becomes transparent. Mix will be cooled to ambient temperatures.

• Mix extracted with 100 ml of pool uppers three times.

• Mix will be extracted with a mild, white, vinaigrette, three times, in 100 ml portions.

• Extracts pooled, rinsed with a lil of that petroleum distillate stuff.

• Solution aqueuse is then dried on a plate under light heat and good air circulation.

• Reekrystelyze?

• Repeat till over 16 g is yielded

Teh analogous N-methyl substitued form
Obtaining teh trippy crack:

• Dissolved in water that has been distilled. Perhaps 100 ml.

• Add soda lime solution till pH >9,<13.

• Extract with 100 ml three times with a mixture of petroleum ether and ethyl acetate.

• Pool washes into the reaction vessel (a large Erlenmeyer flask ~500 ml capacity, not sure exact marked size). Run air over mixture till dry.

This part can be done directly from the vinaigrette solution, without the need to dissolve in dry then dissolve in 100 ml water. Save time and increase yield/purity.

MonoAlkylation of that amino group via methyl halides:

• 16 g of that T is dissolved in 200 ml 91 % pharmaceutical grade rubbing alcohol (perhaps dry to around 99%, but I don't think it's necessary).

• Add 6 ml of iodomethane.

• Let sit for 16 hours, at room temperature.

• Stir for 8 hours, at room temperature.

• Reduce to ~50 ml, under stream of air (these elves don't have vacuums)

Reductive propylating the amine with Ni catalyst and 'Tone:

• Dissolve in 100 ml dimethyl ketone. Let sit.

• Add muriatic acid solution that is pH >4, <6, 100 ml.

• Pour over x grams of Urushibara nickel in a 500 ml 3-neck RB flask, with a thermometer, a glass stopper, and a balloon attached to the necks.

• Run rubber tubing into RV, seal, perhaps put air stone on end of tube?

• Attach to H2 generator (this will be done on top of a mountain, in Africa, to reduce risk of explosion and angering of the native people)

• Gas for x? hours.

• Filter off catalyst.

• Lyse till pH>8,<11

• Extract with ether of petroleum.

• Gas it up.

SOWADDAYATINK?

^They've modified the procedure since, but that's it from the general perspective.

[Xtal]

Yeah... like mother always said, if something sounds too good to be true, then it probably is. But thanks everybody anyways for the feedback. My friend definitely feels totally informed now.

P.S. Personally, my friend would never work with anything that gets reduced by a mercury amalgam... that he plans on ingesting. BAD Bad stuff. I'm sure there are safer methods out there... like the cyanoborohydride pathway referenced on rhodium.

Also... it seems maybe you yanks out there will get zapped with the analouge act if purchasing n-methyltryptamine or even tryptamine (god how I hate the pompous DEA... not even us canucks here can escape from their influence) in bulk from (god forbid) a Chinese supplier, otherwise it would definitely save the trouble of having to go from tryptophan to nMT or T... from a pure economical perspective of course. Since I don't live in the US of A, I can't imagine how difficult it must be to obtain organic reagents, redox regents and solvents without the DEA traumatically traumatizing one's colon.

[stateofhack]

Nothing wrong with aluminium amalgam. The merury wont go into the organic layer...but still do a few washes.

Also using the cyanoborohydride is NOT safer.

[Xtal]

Well haha my friend hates how it boils down to either mercury or HCN... maybe some triacetoxyborohydride will do the trick... but that'll require some expensive un-OTC solvents like THF or acetonitrile.

The other pathway on the rhodium site:
General Procedure for the preparation of N,N-Dimethyltryptamines1

To a cooled (-2°C) and stirred solution of a substituted amine (7.0 mmol), NaCNBH3 (14.0 mmol), and glacial acetic acid (35.0 mmol) in MeOH, a soln of CH2O (38% w/v aq. sol.) in MeOH was added dropwise over 17 min. After 20 min of stirring at 0°C and 2.5 h at room temp, saturated aqueous K2CO3 was added and the MeOH was removed under vacuum. The residue was diluted with H2O and the product was extracted with EtOAc twice, washed with satd NaCl twice, dried, and concentrated. Yield of substituted DMT = 83%.

Also seems pretty promising, and has the added advantage of being specifically used as perhaps a standard procedure for the reductive dimethylation of Tryptamine, tried and proven. My friend thinks he can modify the workup a little to make it easier for those who aren't inclined to purchase expensive vacuum distillation equipment (such as a vacuum aspirator) or chromatography columns. The proposed workup is as follows:

Once the MeOH solution is finished reacting, Aqueous NaOH is added to neutralize the tryptamine salts and any excess Acetic Acid, and to raise the pH to somewhere around 12 or 13. Then the solution is extracted 3 times with naptha, which my friend would imagine, the bigger the alkyl groups are on that teriary amine, the more of it will dissolve in the naptha... and contamination of unreacted tryptamines and mono alkylated tryptamines would be insignificant, given their logPs and relative hydrophilicity. The organic extracts are pooled and washed with aqueous Na2CO3 and then extracted 3x with aqueous HCl. The aqueous extracts are then neutralized and basified with NaOH and extracted 3x with Naptha. The organic extracts are pooled and evaporated to afford some nice xtals.

So... do you think my friends train of thought is sound? Or is he just rambling on again?

[atara]

Originally Posted by stateofhack

Also using the cyanoborohydride is NOT safer.

That should be obvious whenever the prefix "cyano" is involved. Would triacetoxyborohydride work just as well?

Borohydride refs, from borate:

Originally Posted by wikipedia

Sodium metaborate can be hydrogenated back into borohydride fuel by several different techniques, some of which require nothing more than water and electricity or heat. These techniques are still in active development.

http://www.sciencedirect.com/science...5e3468e2af121d

In this paper, we investigated the effects of hydrogen pressure, reaction temperature and transition metal addition on sodium borohydride synthesis by the reaction of sodium meta-borate with Mg and H2. It was found that higher H2 pressure was beneficial to NaBH4 formation. The increase in reaction temperature first improved NaBH4 formation kinetics but then impeded it when the temperature was raised to near the melting point of Mg. It was also found that some additions of transition metals such as Ni, Fe and Co in the NaBO2+Mg+H2 system promoted the NaBH4 formation, but Cu addition showed little effect. The activation energy of the NaBH4 formation from Mg, NaBO2 and H2 was estimated to be 156.3 kJ/mol NaBH4 according to Ozawa analysis method.

They didn't mention the reaction conditions, which could be impossible to obtain. Electrolysis might be possible, but molten salts are hard to handle...

http://www.hydrogen.energy.gov/pdfs/.../vi_b_1_wu.pdf

All three pathways showed excellent progress over the first year. Regarding the first pathway, borates were reduced to BH4 in a molten salt medium, and the presence of BH4 was demonstrated by nuclear magnetic resonance (NMR) spectroscopy. In our knowledge, this is the first example of a one-pot electrolysis process leading from borate to borohydride that has been verified by spectroscopic observation of the product. An NMR spectrum of BH4- ions generated from B2O3 in a molten halide melt is shown in Figure 1. More detailed reports on this reaction can be found in Millenium Cell, Inc. (MCEL) quarterly reports dated October 31, 2005 and January 31, 2005.

http://www.wipo.int/pctdb/en/wo.jsp?...5&DISPLAY=DESC

[BungHole]

Well the elves really fucked up.

They just began a DET synthesis. They did a conversion wrong. They needed to add 0.2 moles of ethyl bromide, 21.8 g. They converted the weight measurement to volume, but instead of dividing the weight by the density of the chemical, they multiplied, and instead of adding ~15 ml, they thought they were suppose to add 32 ml. They only had 23, so they figured a 1.5:1 ratio ethyl bromide:tryptamine would have to do. Then they realized their mistake when going over the math again.

Any body have any advice how the elves can avoid yielding exclusively quaternary salt?

[fcknut]

Originally Posted by BungHole

Well the elves really fucked up.

They just began a DET synthesis. They did a conversion wrong. They needed to add 0.2 moles of ethyl bromide, 21.8 g. They converted the weight measurement to volume, but instead of dividing the weight by the density of the chemical, they multiplied, and instead of adding ~15 ml, they thought they were suppose to add 32 ml. They only had 23, so they figured a 1.5:1 ratio ethyl bromide:tryptamine would have to do. Then they realized their mistake when going over the math again.

Any body have any advice how the elves can avoid yielding exclusively quaternary salt?

In the TIKHAL entry, it seems that 3 equivalents of the halide and base are used, relative to the tryptamine. I would guess that keeping the 1:1 relationship of the halide and base would probably minimise your problems.

Dunno though really...

[BungHole]

Originally Posted by fcknut

In the TIKHAL entry, it seems that 3 equivalents of the halide and base are used, relative to the tryptamine. I would guess that keeping the 1:1 relationship of the halide and base would probably minimise your problems.

Dunno though really...

Yeah, they read in the DET entry he uses the same ration they did, so they said fuck it and stopped worrying about it. Maybe it will have positive results for all they know.

[BungHole]

I have a story that should be useful for endeavors such as these:

The elves have been going about alkylating tryptamine various ways, by both alkyl halides and by reductive alkylation. They chose crystallization of the hydrochloride salt from the freebase dissolved in acetone as the final purification step. Although they had dissolved what was once a clear, yellow oil, a dark solution was always the result. At first, while doing this to product from the alkyl halide method, they assumed impurities were from this specific route were to blame. A large batch of DET was synthesized, and resulted in several grams of product. But this was ruined and wasted by the faulty purification process. A great loss indeed. Then the reductive alkylation was attempted, only to obtain the same results. It was determined that hydrochloric acid, not the route itself, was to blame.

Upon crystallization from anhydrous acetone and freebase using alcoholic tartaric acid, adequate product was obtained. This is the way to go.

A great cost for such valuable knowledge, but I'm so glad I have finally found it....

[stateofhack]

Well that is nice to know

Thank you very much for this bit of info!

[Gusie]

Hi guys. A buddy of mine recently succeeded in decarboxylating some tryptophan by refluxing several grams in about an ounce of spearmint oil (he has a cheap source) for an hour or so. Some toluene was added to the flask and it was all gassed with anhydrous HCL only to precipitate some loose oily crap. After washing a few times with pet. ether, relatively pure tryptamine hcl was recovered (m.p about 250).

So, he plans on feeding most of the stuff to his mexican sclerotia, but is also interested in using some to experiment with zinc catalyzed alkylation..

He's not too too worried about the products specifically, more just poking around with succeeding at all with such a reaction. Given acetone is easier to obtain, it seems like the obvious choice to shoot for the n,n diisopropyl derivative.

My question is: how likely is it that the sterics of 2-propanone will interfere with a zn catalyzed reductive amination of this sort? The only journal reference I've seen for the procedure used only formaldehyde, and made no mention of the efficacy with larger aldehydes/ketones.. Think its more worthwhile to pursue the formaldehyde?

[BungHole]

Originally Posted by Gusie

Hi guys. A buddy of mine recently succeeded in decarboxylating some tryptophan by refluxing several grams in about an ounce of spearmint oil (he has a cheap source) for an hour or so. Some toluene was added to the flask and it was all gassed with anhydrous HCL only to precipitate some loose oily crap. After washing a few times with pet. ether, relatively pure tryptamine hcl was recovered (m.p about 250).

So, he plans on feeding most of the stuff to his mexican sclerotia, but is also interested in using some to experiment with zinc catalyzed alkylation..

He's not too too worried about the products specifically, more just poking around with succeeding at all with such a reaction. Given acetone is easier to obtain, it seems like the obvious choice to shoot for the n,n diisopropyl derivative.

My question is: how likely is it that the sterics of 2-propanone will interfere with a zn catalyzed reductive amination of this sort? The only journal reference I've seen for the procedure used only formaldehyde, and made no mention of the efficacy with larger aldehydes/ketones.. Think its more worthwhile to pursue the formaldehyde?

Go with the isopropyl for any acidic reductive alkylation. The sterics aren't much of a problem, just push the reaction as hard as possible with a low pH and avoid dilution of the solvent by water. Glacial acetic acid and an excess of anhydrous acetone, dissolve the tryptamine, then add zinc powder.

In the OP, note the mention of beta-carbolines. Acidic conditions cause a Pictet-Spengler reaction. Basically, any aldehyde which is reductively aminated by tryptamine will form a ring closure between the 2-position and the amine attached to the ethyl chain. In the case of formaldehyde, it will form tryptoline, which is a pretty strong MAOI. Not something you want to take while assuming it's DMT.

[Gusie]

Ah, good to know thank you.

My friend says he'll probably give the rxn a shot sometime in early september as he's fairly busy up until then. Will post any results back here for sure.

[Xtal]

Haha. Holy crap. I thought this thread was dead. Good to know that the bees out there are making strides in the field of tryptamine chemistry. Too bad SWIM is too broke to afford expensive glassware and doesn't have a credit card for them precursor purchases

[HeaT]

On the topic of sourcing borohydride (cyanoborohydride, too!) look around at photochemical suppliers

[Ford Prefect]

Originally Posted by Gusie

My friend says he'll probably give the rxn a shot sometime in early september as he's fairly busy up until then. Will post any results back here for sure.

Post up nigga.

[atara]

Out of curiosity, did you ever try to make diisopropylethylamine (Hunig's base)? How did it go?

[Gusie]

Hey, sorry- been pretty busy lately.

Anyways, I did get a chance to try this about a month ago.. well, sorta. Just ran it according to the pdf I had available- 500mg trypt(was all I had) added to about 10ml of 12%acetic as I was worried about hydrogen evolution. 4x molar eq. acetone added and stirred in well followed by 4x molar eq. zinc. A decent amount of hydrogen still seemed to evolve from the solution, which was left over light heat for a period of several days, after which the rxn seemed over (there was however still a decent amount of unreacted zinc )

Really, it just might have worked, but i beefed it bigtime on the work-up. Thought I boiled the 'tone off completely but upon bassification big white fluffy clouds of what i assume was aldol came crashing down

Perhaps I'll get the chance to give it another shot sometime soon, but I've been quite distracted helping a friend of mine with some "pseudo" nitrosites- interesting stuff!

[beaker]

Originally Posted by fcknut

Reductive amination with sodium borohydride is a pretty standard procedure...

And the reason yields of amine alkylation with alkyl halides tends to be low, is more to do with formation of quaternary salts, IIRC...

correct, boro is nothing new and there are aqueous procedures with boro as well. same with the alkyl halides, forget it, does not work for dmt, search the literature, that reaction makes a pot full of bugger shit all. fucknt is right, its for quat prep. if there was an easier way than the formaldehyde alkylation believe me it would show up in the literature.

[Gusie]

Just a quick thought-

Has anyone considered performing this reduction electrochemically with the aldehyde/ketone of choice? Yields would most likely be low until the correct electrolyte/electrode conditions are found, but seems to me it's a worthy cause.

Come to think of it I haven't seen much about electrochemical reductive alkylation for tertiary amines.. Any reason this wouldn't work?

Will search the literature some more soon..

[stateofhack]

Electrochemical reductions are interesting, but i had a hard time finding the materials of appropriate size and type! They do also need some bit of testing at the beggining but yes one its set up its very neat and saves a lot of steps, working up etc

[Gusie]

Ok.. my pal gave this whole zinc thing another go round with a little bit more care and consideration. Basically same reaction starting with 3grams relatively pure tryptamine hcl: added base, extracted with heptane(possibly a poor solvent choice which may explain the yields), filtered, washed with dH2O and gassed with anhydrous HCl to yield maybe 200mg of off-white yellowish solid (he didn't weigh it yet). This was recrystallized from the minimum amount of boiling MEK and filtered to yield a very small amount of shiny white solid.

Here's the predicament: this very nice shiny white solid which he was so hoping was the intended compound has a melting point of 154-155C . It's a sharp one too. Literature reports the di-isopropyl derivative at 192-193C..

Now, I don't know what this stuff is exactly, but I aint putting in my nose or nothin' till I know it's good for me...

So, does anyone have mp data on nIPT? Couldn't seem to find anything in the literature but I'll have a looksie

Nvm, I guess there is a tihkal entry -.- 224-227C... So what is this stuff? The beta-carboline perhaps?

[Xtal]

Lol, hey good work man. I guess the only way to know if you got the real yay-yay is to try it (or if that's not possible give it to some rats... )

[Gusie]

mmm.. some rat took about 30mg in a capsule a couple days ago. A mild stimulation was definitely noticed from 1-4 hrs, but it was also out picking wild psilocybes almost the whole time so that may have had something to do with it.. My guess is that this produced a mixture of nipt and dipt rather than a solely di-substituted product, which would make sense given the extremely low yields and difference in melting point from literature values.

Anyways, pretty much out of material from that after the re-xtalizing and that one somewhat disappointing trial. Considering putting the rest of the tryptamine towards a haloalkane style alkylation with carbonate.

Anyone have thoughts as to whether the chloro-alkanes would be sufficiently reactive for this? They seem to have a much nicer toxicological profile than the bromos..