Potassium Carbonate → 3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propan-1-ol

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 3-bromo-propanol (5.9 mL, 65.4 mmol) in acetonitrile (500 ml) was added Nal (19.6 g, 131 mmol) and K2CO3 (18.1 g, 131 mmol). The mixture was stirred at 85° C. for 1 h, and then N-(2,2-diphenylethyl)-N-(2-chloro-3-trifluoromethyl-benzyl)amine (34.0 g, 87.2 mmol) was added. The reaction mixture was heated at 85° C. overnight. Solvent was removed, the residue was washed with H2O, and extracted twice with EtOAc. The EtOAc extracts were dried over Na2SO4, filtered, and concentrated. The crude mixture was purified by silica gel chromatography (35 g Redisep column, silica, 40 um, 60 Å, 35 mL/min, A: hexanes, B: EtOAc, B: 0% for 2 min, B: 0% to 10% over 10 min; B: 10% for 2 min; B: 10% to 20% over 15 min; B: 20% for 2 min; B: 20% to 30% over 40 min; detection at 214 nm) to give 13.3 g (29.7 mmol, 34%) of the title compound as a white solid. 1H NMR (CDCl3, 400 MHz) □: 7.6 (d, J=7.6 Hz, 1H), 7.3-7.1 (m, 12H), 4.2 (t, J=7.6 Hz, 1H), 3.8 (s, 2H), 3.6 (t, J=5.6 Hz, 2H), 3.2 (d, J=7.6 Hz, 2H), 2.8 (t, J=6.0 Hz, 2H), 2.5 (s, 1H), 1.7 (m, 2H);

Provenance & Evidence