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

1992 
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.
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