The Hive > Tryptamine Chemistry

Indole Grignards

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Here are some references in addition to Post 8809 (Lilienthal: "Re: maybe 4 steps from tryptophan to DMT/DET/DPT", Tryptamine Chemistry):

Chem. Ind. 1388 (1964) dialkyltryptamines
J. Chems. Soc. 2220 (1967) dialkyltryptamines
Patent US2692882 5-benzyloxy-indole-3-acetamides
Patent US2703325 5-benzyloxy-indole-3-acetonitriles __> 5-benzyloxy-tryptamines
Patent US2728778 5-benzyloxy-indole-3-acetonitriles

See also Patent US1793176 (2-methyl indole MgX (grignard reagent) reacted with ClCH2CH2N(CH3)2 to get 2-methyl DMT; example 6).

Patent US4017513 looks interesting.  I wonder if it could work for IAA and dimethylamine.

Re: Patent US4017513

I don't see what is there that is patentable.

It seems like nothing but prior art. They use the ion exchange resin as a strong acid catalyst to form the methylester of the amino acid then they remove the resin, add ammonia and perform the ammonolysis of the ester.

Sure this should work for IAA + dimethylamine.

Not necessarily it should work very well for IAA/Me2NH, dimethylamine generally reacts quite sluggish with esters (if at all)


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