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The Hive => Tryptamine Chemistry => Topic started by: SPISSHAK on September 01, 2002, 08:03:00 PM

Title: Tryptamine alkylation question?
Post by: SPISSHAK on September 01, 2002, 08:03:00 PM

I read in Shulgin's book 'TIKHAL' that he alkylates tryptamines with different alkyl halides like bromoethane, methyl iodide.
But he frequently uses di-isopropyl ethylamine as a proton acceptor.
And I was wondering why he does'nt use triethylamine, like they use as a proton acceptor in acyalation reactions involveing acyl halides.
I therorize that the two isopropypl groups sterically interfere with tetra-alkammonium halide formation, from the alkyl halides present in the system, which would be an unwanted variable in this system.
Anyone have any insight?

Title: Steric hindrance.
Post by: terbium on September 01, 2002, 08:57:00 PM

I therorize that the two isopropypl groups sterically interfere with tetra-alkammonium halide formation, from the alkyl halides present in the system, which would be an unwanted variable in this system.
Yes.

Post 302559 (https://www.thevespiary.org/talk/index.php?topic=13331.msg30255900#msg30255900)

(Rhodium: "base", Tryptamine Chemistry)