Collect. Czech. Chem. Commun. 1987, 52, 182-191

Preparation of 2,2,6,6-tetramethyl-4-aminopiperidine and its substituted compounds by electroreduction of azomethines of 2,2,6,6-tetramethyl-4-oxopiperidine (triacetonamine)

M. Ya. Fioshin, I. A. Avrutskaya, I. I. Surov and V. T. Novikov

D. I. Mendeleev Institute of Chemical Technology, Moscow, U.S.S.R.


Five methods have been developed for electrosynthesis of 2,2,6,6-tetramethyl-4-aminopiperidine in 95-98% yield via the lead-cathode reduction of 2,2,6,6-tetramethyl-4-oxiimino-piperidine, a mixture of triacetonamine with inorganic salts of hydroxylamine, and a mixture of triacetonamine with nitric acid in a solution of sulphuric acid, via the reduction of azine triacetonamine and of a mixture of triacetonamine with inorganic salts of hydrazine in a neutral solution. The corresponding saturated derivatives of 2,2,6,6-tetramethyl-4-aminopiperidine have been obtained in 60-80% yield by electroreduction of phenylimine and ethylene diimine.