Tryptamine-> DMT via formamide

[DaCosmos]

I was reading the Tikhal synth for DMT from tryptamnime + ethyl formate-> formamide, then an LAH reduction. Any foreseen pitfalls besides the obvious..ie long reaction time, LAH..Also was thinking about sodium cyanoborohydride instead..Comments?

[Lilienthal]

I heard that is a horrible reaction from N-formyl-tryptamine to N-methyltryptamine. In THF at reflux you will get low yields and a high amount of byproduct (possibly skatole). At lower temperatures in refluxing ether / THF you will get a chewing-gum-like mass which can't be stirred.

[DaCosmos]

Well what do you think the best method is. I know "best" is a subjective term. For my purposes it's 1. Chance of success 2. Availabilty of chemicals. I've read all of it. Breath of Hope, tryptophol, standard oxalyl chloride, IAA etc..And I'm still lost on even what SWIM will attempt. I'm no neophyte to the lab, but I can't even choose. I've tried this honey, HYPERSPACE is the place to be. But it's so scarce SWIM need his own supply. I don't seee many successes in this forum. Pretty much just Drone. Not even lately. Is there a method that doesn't give an assload of tar (formamide), good success record (Breath does not), or too many intermediates (oxalyl)??..SWIM has no problem with extended reaction times as long as it doesn't stink. SWIM is just looking for a method with a "reasonable" chance of success. All input is appreciated. Thanks for the feedback Lil.

[Lilienthal]

1. Tryptophol route
2. Aminobutyraldehyde route. See:

useful tryptamine methods

(http://hive.lycaeum.org/wwwthreads/perl/showflat.pl?Cat=&Board=tryptamine&Number=17677&page=1&view=collapsed&sb=5).
3. Anthony-Speeter route with oxalylchloride / alanate (use dry solvents and distill the products)

All these routes are bad for secondary tryptamines (but you may use N-benzyl protection).