A solution of N-(3,5-dichlorobenzyl)-1-(4-fluorophenyl)methanamine (0.5 g, 1.76 mmol), EDCI.HCl (0.47 g, 2.46 mmol), 3-(Boc-aminomethyl)benzoic acid (0.53 g, 2.11 mmol) and HOBT.H2O (0.16 g, 1.06 mmol) in DMF (8 mL) was stirred at rt for 20 h. The residue was diluted with ethyl acetate and 1 N HCl solution. The organic layer was separated, washed with 1N NaOH solution, brine, dried over MgSO4, concentrated and the residue was purified by flash chromatography on silica gel (Eluent: A: CH2Cl2, B: ethyl acetate; condition: 100% A to 15% B. (35 min gradient) to obtain the desired product as a white solid (0.81 g, 89%). 1H NMR (CDCl3): δ 7.42-7.32 (m, 5H), 7.17-6.99 (m, 6H), 4.88-4.63 (m, 2H), 4.42-4.35 (m, 4H), 1.47 (s, 9H).
