Aminoalkylation of metal derivatives of indole. Part III. Alkylation of lithio-derivatives of N-substituted indoles with 1-chloro-2-dimethylaminoethane

Abstract

1-Methyl- and 1-phenyl-indolyl-lithium, when treated with 1-chloro-2-dimethylaminoethane, underwent aminoalkylation at the 2-position of the indole nucleus whereas the lithio-derivatives of 1-benzyl- and 1-benzyl-3-phenylindole yielded products derived by substitution at the α-position of the benzyl group. The structures of the amines were confirmed by ¹H n.m.r. spectra and by hydrogenolysis experiments. The syntheses of 1-phenyl- and 1-benzyl-3-phenyl-indoles are described.