The Hive > Tryptamine Chemistry

Clarke-Eschweiler reaction

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PEYOTE:
To obtain N,N-dimethyl alkanes form R-NH2, you can use the reaction of Clarke-Eschweiler
using HCOOH and CH2O in polymeric form....

Rhodium:
This won't work with tryptamine. Formaldehyde and acid will lead to a pictet-spengler cyclization, forming a beta-carboline.

http://rhodium.lycaeum.org

Lilienthal:
But not for tryptamines, since they will cyclize to beta-carbolines under this conditions (Pictet-Spengler reaction)  :( .

PEYOTE:
I'd like to know more of this cyclization..... thanks...

Rhodium:
Like this, http://home.ici.net/~hfevans/reactions/RXN300.htm but instead the new carbon-carbon bond is formed between the formaldehyde imine and the 2-position of the indole nucleus.

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