3,4-Dimethoxyphenethylamine to tryptamine :)

mk-1 · Tue Apr 05, 2005 4:56 pm

Hi fellas...
apprently 3,4-dimethoxyphenethylamine hydrochloride can be transformed to tryptamine in good yields (81%) with only aqueous NaOH and H2O2.
heres the ref -
KODATO SHINICHI; SUGASAWA SHIGEHIKO:
DEFORMYLIERUNG VON FORMAMIDEN.
PROC. JAP. ACAD., 1980, B 56, NO 9, 576-578

thought ud linke to know Smile

Aleister · Thu Apr 21, 2005 7:25 pm

Do anyone have any idea how this works? I'm not that knowledgeable in chemistry yet, and i'm trying to understand reaction mechanisms. This doesn't seem to make sense though. any helps appreciated Smile

mk-1 · Thu Apr 21, 2005 8:08 pm

truely i dont have any idea how this actually takes place, but the reaction is pictured like this -

demorol · Fri Apr 22, 2005 12:24 am

Where does the nitrogen in indole ring come from?

Nicodem · Fri Apr 22, 2005 2:03 am

Just taking a reaction scheme out of SPRESIweb database without checking the paper itself does not means much. There are several mistakes in that database, sometimes two steps are integrated in a single reaction, very often some of the reagents are missing or the conditions are not given.

Since that reaction makes no sense whatsoever I would advise to ignore it untill someone is willing to retrieve the paper.

Aleister · Fri Apr 22, 2005 2:51 am

the indole ring could be formed by cyclization of the ethyl amine chain maybe? but that doesn't really explain anything else like what happens to the methoxy groups or where the rest of the tryptamine skeleton comes from.