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An Efficient Preparation of 1,2-Diamino-1-phenylheptane
Organic Chemistry Laboratory, Central Leather Research Institute, Adyar, Chennai – 600 020. Tamil Nadu, India
* Author to whom correspondence should be addressed.
Received: 12 December 2001; in revised form: 24 June 2002 / Accepted: 25 June 2002 / Published: 30 June 2002
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.
Keywords: Piperidinone; Schmidt rearrangement; Hexahydrodiazapinone; Vicinal diamine
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Thennarasu, S.; Perumal, P.T. An Efficient Preparation of 1,2-Diamino-1-phenylheptane. Molecules 2002, 7, 487-493.
Thennarasu S, Perumal PT. An Efficient Preparation of 1,2-Diamino-1-phenylheptane. Molecules. 2002; 7(6):487-493.
Thennarasu, S.; Perumal, P. T. 2002. "An Efficient Preparation of 1,2-Diamino-1-phenylheptane." Molecules 7, no. 6: 487-493.