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Paper | Regular issue | Vol 27, No. 12, 1988, pp.2883-2890
Published online, 1st January, 1970
DOI: 10.3987/COM-88-4749
Synthesis of 2-(4-Piperidylmethyl)indoles. Intermediates for the Synthesis of Strychnos Alkaloids

Josep Bonjoch,* Josefina Quirante, Ana Linares, and Joan Bosch*

*Laboratory of Organic Chemistry, , Faculty of Pharmacy, University of Barcelona, Av. de Joan XXIII, s/n, 08028 Barcelona, Spain

Abstract

The synthesis of 2-[(cis-1-benzyl-3-ethyl-4-piperidyl)-methyl]indole (6) by three alternative procedures is reported, the condensation of the organodilithium derivative of N-trimethylsilyl-o-toluidine with ethyl cis-1-benzyl-3-ethyl-4-piperidineacetate (1) being the most efficient method. The indole derivative 6 has been converted into azocinoindole 7 by oxidative cyclization with mercuric acetate and into piperidylmethylindole 8 by debenzylation. Compounds 7 and 8 are known intermediates in previous syntheses of the Strychnos indole alkaloids tubifolidine and tubifoline.