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clearly_not_atara
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Not sure if this is actually a legal (w/r/t the rules) discussion, but since DMT is far more easily extracted, I guess it doesn't count.
IMO you should use methyl oxalate or methyl carbonate or a similar "weak" methylating agent that won't quaternize the tryptamine. Evades all
possibility of a Pictet-Spengler. Methyl oxalate is such a good candidate that I'm not sure anything else is worth mention... trimethylsulfonium
bromide, maybe.
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Pumukli
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Is methyl-oxalate a methylating agent?
I think it would rather acylate the primary amine yielding tryptamine-oxalyl-amide and methanol.
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nlegaux
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You could perform a Hofmann rearrangement using the tryptamine. It would remove the α-carbon shortening the chain by one, but I am not certain how it
would behave with the secondary amine in the heterocyclic ring.
nlegaux
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careysub
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Quote: Originally posted by zed  | | Ummm. I've heard that the reagent isn't easy to come by. And, making it involves using HCN. Not fun. |
It appears that sodium cyanoborohydride can be prepared without ever having free HCN by:
1. making mercury(II) cyanide from mercury(II) oxide and potassium/sodium cyanide*.
then
2. making cyanoborohydride from sodium borohydride and mercury(II) cyanide
Not without its own hazards, and I am not sure that if you have excellent fume handling equipment that it is any safer than HCN.
(*Which can be made in a laboratory crucible using sodium metal and ferrocyanide.)
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nlegaux
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Something else that can be done is a Pictet-Spengler reaction allowing for the creation of interesting heterocycles. All that is required would be the
tryptamine, an aldehyde or ketone, and an acid catalyst.
nlegaux
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Noshtuba
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careysub do you know of any sources documenting the procedure with mercury cyanide?
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lullu
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Reductive amination works with plain NaBH4 when done right.
Also there are a lot of better alternatives to NaBH3CN that are easily prepared and that won't reduce your aldehyde and will work at pH 5.
Have a look at substituted pyridine boranes for example.
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careysub
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B. Gyori and G. Emri; J. Chem. Soc., Chem. Commun., 1983, 1303.
Referenced here (pg. 7):
http://cora.ucc.ie/bitstream/handle/10468/1656/MyersM_PhD198...
I do not have the original Gyori and Emri article.
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Cloner
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15.1g tryptamine was added to 300 ml shellsol d70 and refluxed with 2.5g spearmint oil. The resulting mixture became beer colored after about 30´.
During the operation of the reflux, gas evolved that did precipitate CaOH solution.
However, a wet PH paper held in top of the reflux column did color blue, not red. This is very strange. Could it be NH3? It isn't a good sign at all.
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Pumukli
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Tryptamine? Wasn't it tryptophane?
(Cloner, your reaction seems to be a decarboxylation attempt. Am I mistaken?)
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Cloner
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yes, you are of course right.
I started to wonder if it could be tryptamine itself that is slightly volatile...
[Edited on 16-9-2015 by Cloner]
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