1-Chloro-4-(chloromethyl)benzene → 3-Amino-1-(4-chlorobenzyl)homopiperidine

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p-Chlorobenzyl chloride (463 mg, 2.9 mmol) and K2CO3 (828 g, 6 mmol) were added to an acetonitrile (45 mL) solution of 3-aminohomopiperidine (1.71 g, 15 mmol), and the resulting mixture was stirred at 70° C. with heating for 9 hours, cooled to 25° C. and concentrated to afford a yellow solid. The resulting residue was partitioned between H2O (5 mL) and ethyl acetate (50 mL) and the aqueous layer was extracted with ethyl acetate (50 mL×2). The organic layers were combined, washed with brine (20 mL), dried (over MgSO4) and concentrated. The obtained yellow oil was purified by column chromatography (SiO2, 5-20% methanol/dichloromethane gradient elution) to afford the objective compounds as yellow oil (639 mg, 93%).

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