4-tert-Butylcyclohexanone → HCID 178445680, compound

Participants

Reaction Steps

Equimolar amounts of 4-tert-butylcyclohexanone and benzylamine or 1-phenylethylamine are vigorously stirred in the solvent in question in the presence of a catalyst and in an atmosphere of pure hydrogen. Once no more benzylamine or 1-phenylethylamine can be detected by taking samples, 200 ml of ethyl acetate are added if the solvent used is ethylene glycol. The reaction mixture is washed three times with water, filtered, dried over MgSO4 and concentrated under reduced pressure. If other solvents are used, the reaction mixture is filtered off directly after the reaction has ended, the catalyst is washed with methanol and the filtrate is concentrated under reduced pressure. In each case, the crude product has the cis-selectivity stated in Table 1 (determination by HPLC). Crystallization of the hydrochlorides or purification by column chromatography (silica gel, ethyl acetate) gives pure N-benzyl-cis-4-tert-butyl-cyclohexylamine or pure N-(1-phenylethyl)-cis-4-tert-butyl-cyclohexylamine.

Provenance & Evidence