Sodium Hydroxide → HCID 178444679, compound

Participants

Reaction Steps

To a solution of 4-(3-(2-(benzylsulfanyl)-1H-imidazol-4-yl)phenyl)-1-hexyl-3,4-dimethylpiperidine (Example 51, 98 mg, 0.21 mmol) in ethanol (2 mL) at room temperature was added 1 N NaOH (1.5 mL) and Raney® nickel (0.5 g, 50% slurry in water). The reaction was stirred for 5 minutes and then filtered through Celite®, washing with ethanol. The filtrate was concentrated in vacuo and the residue was dissolved in ethyl acetate (5 mL). The organic layer was washed with saturated aqueous sodium hydrogencarbonate (5 mL), dried over MgSO4, filtered and concentrated in vacuo. The residue was then purified by column chromatography on silica gel eluting with ethyl acetate:0.88 ammonia (100:1) and then ethyl acetate:methanol:0.88 ammonia (70:30:1). The title compound was obtained as a clear oil (13 mg, 19%).

Provenance & Evidence