Stereochemistry of the reactions of cyanohydrins of substituted 4-piperidones with ammonia and amines. Synthesis and structure of substituted 4-amino-, 4-methylamino-, and 4-dimethylamino-4-cyanopiperidines

The action of ammonia, methylamine, or dimethylamine on substituted 4-hydroxy-4-cyanopiperidines in a modified Strecker synthesis gave mixtures of stereoisomers of the corresponding 4-amino-, 4-methylamino- and 4-dimethylamino-4-cyanopiperidine. ¹H and ¹³C NMR spectroscopy was used to determine the structure of these products. Unusual stereocontrol was found for the reaction of methylamine and dimethylamine with cyanohydroxypiperidine with substituents at C₍₂₎ and C₍₅₎ in the ring.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1621–1627, December 1992.