1-Chloro-4-(chloromethyl)benzene → {[1-(4-Chlorobenzyl)piperidin-4-yl]methyl}amine

Participants

Reaction Conditions

Reaction Steps

A solution of 4-(aminomethyl)piperidine (7.00 g, 61.3 mmol) in CH3CN (100 mL) was treated sequentially with K2CO3 (3.02 g) and 4-chlorobenzyl chloride (3.52 g, 21.8 mmol). The reaction mixture was heated to 60° C. for 16 h, cooled to 25° C. and concentrated. The residue was partitioned between CH2Cl2 (75 mL) and water (50 mL), and was washed with water (2×50 mL) and brine (1×50 mL). The organic phase was dried (MgSO4) and concentrated. Chromatography (SiO2, 4% H2O-iPrOH) afforded4-(aminomethyl)-1-(4-chlorobenzyl)piperidine (3.58 g, 69%).

Provenance & Evidence