Alkylating tryptamines...

[jim]

I have heard a lot of discussion that DRONE's suggestion of using PTC conditions and a slight excess of MeX won't work for tryptamines.

What is the consensus?

Does it, or doesn't it?

[Acme]

Surely a few bees have tried and failed.  Only Drone can say for sure, and off to where he has gotten of late I do not know.

[abc123]

Jimbo,

Why the method is bunk even W/ PTC's is because you yeild the quaternary ammonium salt of said product. Once that happens "a done bun can't be undone". Every attempt made by any of my sources (from Shulgin to Calamus and the rest of the B's)to try to decompose this into the desired active "goodies" have either failed or resulted in piss poor yeilds not even worth bothering to mention. From calculated bond enthalpy you can tell that the process is irreversable do to loss of Gibbs free energy. Entropy is such a bitch!

Yours in science

Calamus

[Acme]

Maybee you should check p 412 of TIHKAL.  Shulgin uses LiEt₃BH

[foxy2]

They used to talk of ethanolamine being able to transform the quanternary amine salt to dimethyl amine however I have yet to hear anyone verify it or post a good reference.

Anyone know about this ethanolamine demethylation?
Tried it? Successfully or Unsuccessful?
Have a reference for it?

Somebody has to have attempted this
Do Your Part To Win The War

[Rhodium]

JMC 13, 254 (1970) talks about using 15min reflux with ethanolamine to demethylate a quat.

[jim]

JMC?  I'm sorry my brain must not be working, What does JMC stand for?  Journal of Medicinal Chemistry?

[Rhodium]

You are correct.