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An Efficient Preparation of 1,2-Diamino-1-phenylheptane

Author(s): S. Thennarasu | P. T. Perumal

Journal: Molecules ISSN 1420-3049
Volume: 7; Issue: 6; Start page: 487; Date: 2002;
Original page

Keywords: Piperidinone | Schmidt rearrangement | Hexahydrodiazapinone | Vicinal diamine

ABSTRACT
A convenient four-step method for the preparation of the lipophilic vicinal diamine 1,2-diamino-1-phenylheptane is described. Condensation involving octan-2-one, benzaldehyde and ammonia is reported. Regioselective Schmidt rearrangement of 2,6-diphenyl-3-pentyl-piperidin-4-one (1) to 2,7-diphenyl-3-pentyl hexahydrodiazapin-5-one (3) is presented. Hydrolysis of 2,7-diphenyl-3-pentyl hexahydrodiazapin-5-one to 1,2-diamino-1-phenylheptane (4) is also reported for the first time.