Potassium Cyanide → N-(4-amino-4-cyanocyclohexyl)-4-ethoxy-3-methylbenzenesulfonamide

Participants

Reaction Steps

A 1:1 mixture of concentrated aqueous ammonium hydroxide (28-30%): water (1606 μl, 6.26 mmol) followed by ammonium chloride (223 mg, 4.17 mmol) was added to 4-ethoxy-3-methyl-N-(4-oxocyclohexyl)benzenesulfonamide (Intermediate 122, 650 mg, 2.087 mmol) in methanol. The reaction was stirred for a few minutes then potassium cyanide (272 mg, 4.17 mmol) was added in one portion. After 18 hours the reaction was diluted with dichloromethane and 5N sodium hydroxide followed by water was added to make the aqueous layer pH 12. The aqueous layer was extracted fives times with dichloromethane. TLC (50% ethyl acetate in heptane) suggested a small amount starting material was present, but a major UV spot was just off baseline. Combined organic layers were dried over sodium sulfate, filtered, and concentrated, to yield crude N-(4-amino-4-cyanocyclohexyl)-4-ethoxy-3-methylbenzenesulfonamide (770 mg, 2.282 mmol) which was used without further purification. LCMS [M+H]=338.3.

Provenance & Evidence