2-Chloroaniline → 3-Phenyl-3-cyclohexanepropanamide

Participants

Reaction Conditions

Reaction Steps

A solution of 3-phenyl-3-cyclohexanepropanoic acid (0.5 g, 2.15 mmol) and oxalyl chloride (0.3 ml, 3.01 mmol) in 5 ml of toluene was stirred for 3 hours at 35-40° C. and then at room temperature overnight. The mixture was then concentrated in vacuo to provide a yellow oil which was dissolved in 5 ml of CH2Cl2, cooled to 0° C. and treated with 2-chloroaniline. The resultant mixture was stirred at 0° C. for 2 hours and filtered. The filtrate was then washed sequentially with 1.0N HCl, NaHCO3 and brine, dried over Na2SO4, filtered and then concentrated in vacuo to provide a white solid (0.66 g, 92%). A portion of this solid was recrystallized (hexanes/CH2Cl2) to provide a white solid.

Provenance & Evidence