The Vespiary
The Hive => Tryptamine Chemistry => Topic started by: foxy2 on September 08, 2001, 03:52:00 AM
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This looks very promising!!!
Someone needs to look up these journal articles and post the procedures here. Please
Eschweiler-Clarke Reaction.
2RNH2 + 2HCHO + 2HCOOH __> RN(CH3)2 + 2CO2 +2H2O
W. Eschweiler, Ber. 38, 880 (1905)
H. T. Clarke, H. B. Gillespie, and S. Z. Weisshaus, J. Am. Chem. Soc. 55, 4571 (1933)
Moore, Organic Reactions 5, 301 (1949)
F. Moller, R. Schroter, Methoden der organischen Chemie XI(I), 650 (1957)
R. Baltzly, J. Am. Chem. Soc. 75, 6083 (1953)
A. C. Cope, and W. D. Burrows, J. Org. Chem. 30, 2163 (1965); 31, 3099 (1966).
Do Your Part To Win The War
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This does not work with tryptamines as far as I know. The HCOOH is a strong enough acid to cause the pictet-spengler reaction of the initially formed formyltryptamine to form a beta-carboline.
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Well now ain't that a bummer.
But with such easy to find precursors a 10% or hell even a 5% yeild really wouldn't be to bad at all. DMT could be separated from the betacarbolines by distillation or sublimation, no?
With a 5% yeild you get 5 grams of DMT for possibly less than $100 in supplies. I know 5 grams of DMT would be a lifetime supply for me.
Do Your Part To Win The War
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Talk to Lilienthal, he can probably tell you what the ratio of DMT to beta-carboline that one can expect from a reaction like this. But I would suggest KrZ's route using NaBH3CN instead, he reports 65% yields or more.
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I would expect 100% carbolines and 0% DMT.
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This is just a suggestion pertaining to a modifaction to foxy's new route.... Could subsituting and acid w/ a greater pKa like acetic acid or proponic acid possiably effect the outcome of your predicted results... It's just a thought.... Mabe the acids don't have to mirror the carbonyl compound... Anyway I feel that the procedure should be investigated. Hell it's worth a shot.
Calamus
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For the Eschweiler-clarke reaction to work, the acid must be formic acid, due to its reducing properties. It is a reductive amination, with formic acid as the reducing agent.
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Good point... I always seem to over look the obvious. Every time I hear of a promising route to dialkyltryptamines that dosen't involve metal hydrides or pain in the ass extractions of natural sources, I foam at the mouth and get ahead of myself. Hell we can always keep dreaming....
Calamus
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Okay, I know that you normally shouldn't dabble with shit if you don't what you're talking about, but... AFAIK the methylation as described by Eschweiler was done only with formaldehyde, Clarke later added the formic acid as an activating reagent.
So pardon my blunt ignorance, but couldn't this be something ponder about?
Peace out,
Lord Shadowcaster
Just say know.
Lord Shadowcaster