AMINOALKYLATION OF METAL DERIVATIVES OF INDOLE .3. ALKYLATION OF LITHIO-DERIVATIVES OF N-SUBSTITUTED INDOLES WITH 1-CHLORO-2-DIMETHYL-AMINOETHANE

1-Methyl- and 1-phenyl-indolyl-lithium, when treated with 1-chloro-2-dimethylaminoethane, underwent amino-alkylation at the 2-position of the indole nucleus whereas the lithio-derivatives of 1-benzyl- and 1-benzyl-3-phenyl-indole 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.