O[N:2]=[C:3]1[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:4]1.[ClH:15]>[Ni].C(O)C>[ClH:15].[C:9]1([CH:6]2[CH2:5][CH2:4][CH:3]([NH2:2])[CH2:8][CH2:7]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1A mixture of 1-(hydroxyimino)-4-phenylcyclohexane (17.4 mmol) and Raney Nickel (300 mg) in ethanol was hydrogenated (90 psi) at 50° C. for 40 hours. The mixture was filtered through a pad of Celite, washed with MeOH, and concentrated. The residue was dissolved in MeOH, treated with HCl (4 N in dioxane, 20 mmol), and concentrated to give 4-phenylcyclohexylamine hydrochloride (100%).
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