4-Phenylcyclohexanone oxime → 4-Phenylcyclohexylamine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of Intermediate 13 (5.1 g) and nickel chloride (12.8 g) in methanol (40 ml) at −30° C., was added sodium borohydride (10.2 g). The reaction was stirred at −30° C. for 30 min, before being stirred at room temperature for 16 h. The solvent was removed in vacuo, and the black slurry was dissolved in aqueous hydrochloric acid (2M, 300 ml), and washed with ethyl acetate (3×200 ml). The aqueous layer was then basified to pH 10 using solid sodium hydroxide, and EDTA added until the solution stayed blue. The aqueous was then extracted with ethyl acetate (3×200 ml), the combined organic extracts dried over magnesium sulphate (4 g), and the solvent removed in vacuo to yield the title compound as a white oily solid (3.2 g).

Provenance & Evidence