Potassium Cyanide → HCID 22645388, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-hexyl-3,4-dimethyl-4-(3-trifluoromethanesulfonyloxyphenyl)piperidine (Preparation 1, 500 mg, 1.19 mmol) in 1-methyl-2-pyrrolidinone (2.5 mL) was added to a flask containing potassium cyanide (155 mg, 2.38 mmol). The solution was de-oxygenated by evacuating and flushing with nitrogen three times. Catalytic quantities of palladium(II) acetate and 1,1 ′-bis(diphenylphosphino)ferrocene were added and the reaction mixture was warmed to 60° C., at which temperature it was stirred for 3 hours. The reaction mixture was cooled to room temperature and poured into saturated aqueous sodium hydrogencarbonate solution (50 mL). The product was extracted into ethyl acetate (3×30 mL). The combined organics were dried (Na2SO4) and concentrated in vacuo. The residue was purified by column chromatography on silica gel (15 g) eluted with a gradient of ethyl acetate:hexane:0.880 ammonia (20:79:1 to 50:49:1) to give the title compound as an oil (346 mg).

Provenance & Evidence