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)

• Published in: Collection of Czechoslovak chemical communications Vol. 52; no. 1; pp. 182 - 191
• Main Authors: FIOSHIN, M. YA, AVRUTSKAYA, I. A, SUROV, I. I, NOVIKOV, V. T
• Format: Journal Article
• Language: English
• Published: Praha Czechoslovak Academy of Sciences, Institute of Organic Chemistry and Biochemistry 1987
• Subjects: Chemistry; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Organic chemistry; Preparations and properties; Electrodes; Chemical reduction; Hydroxylamine; Aniline; Ketimine; Lead; Ketoxime; Electrode material; Hydrazine; Electrochemical reaction; Primary amine
• ISSN: 0010-0765; 1212-6950
• DOI: 10.1135/cccc19870182

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.