1-Chloro-4-(chloromethyl)benzene → 2-Carbamoyl-1-(4-chlorobenzyl)pyrrolidine

Participants

Reaction Conditions

Reaction Steps

A solution of dl-prolinamide hydrochloride (2.5 g, 21.8 mmol) in CH3CN (35 mL) was treated with Et3N (7.45 mL) and 4-chlorobenzyl chloride (3.88 g, 24.1 mmol). The reaction mixture was stirred at 70° C. for 4 h and then at 25° C. for 16 h. The resulting mixture was diluted with CH2Cl2 (20 mL) and was washed with water (3×30 mL). The organic phase was dried (MgSO4) and concentrated. Chromatography (SiO2, 1% CH3OH—CH2Cl2) afforded 2-carbamoyl-1-(4-chlorobenzyl)pyrrolidine (5.21 g, 81%).

Provenance & Evidence