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Molecules  2002 

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

DOI: 10.3390/70600487

Keywords: Piperidinone, Schmidt rearrangement, Hexahydrodiazapinone, Vicinal diamine

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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.

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