A simple synthesis of 5-amino-3-(2-dimethylaminoethyl)indole [5-amino-N,N-dimethyltryptamine]

Article abstract of DOI:10.1080/00397919308020402

A short (three step) synthesis of 5-amino-3-(2-dimethylaminoethyl)indole [5-amino-N,N-dimethyltryptamine, 4] from commercially available starting materials is presented. Reaction of 5-nitroindole with oxalyl chloride followed by dimethylamine afforded N,N-dimethyl 5-nitroindole-3-glyoxamide (1), which was reduced by diborane to 5-nitro-3-(2-dimethylaminoethyl)indole (3). Catalytic reduction of (3) afforded the title compound in 19% overall yield from 5-nitroindole.

Full text of DOI:10.1080/00397919308020402

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Synthetic Communications: An
International Journal for Rapid
Communication of Synthetic
Organic Chemistry
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A Simple Synthesis
of 5-Amino-3-(2-
dimethylaminoethyl)
indole [5-Amino-N,N-
dimethyltryptamine]
a
a
a
John E. Macor , Ronald Post & Kevin Ryan
a
Department of Medicinal Chemistry, Central
Research Division, Pfizer Inc, Groton, Connecticut,
06355
Published online: 24 Sep 2006.
To cite this article: John E. Macor , Ronald Post & Kevin Ryan (1993) A
Simple Synthesis of 5-Amino-3-(2-dimethylaminoethyl) indole [5-Amino-N,N-
dimethyltryptamine], Synthetic Communications: An International Journal
for Rapid Communication of Synthetic Organic Chemistry, 23:1, 65-72, DOI:
10.1080/00397919308020402
To link to this article: http://dx.doi.org/10.1080/00397919308020402
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