2-Chloro-N-[2-(4-chloro-phenyl)-ethyl]-acetamide synthesis

Yield:3840-66-2 67%

Reaction Conditions:

with triethylamine;N-ethyl-N,N-diisopropylamine in dichloromethane;acetonitrile at 0 - 20; for 3.5 h;

Steps:

1

To 2-(4-Chlorophenyl)-ethylamine (5 g, 32.1 mmol) in CH₃CN (150 ml) was added Et₃N (5.4 ml, 38.5 mmol) at 0° C. under a N₂ atmosphere followed by chloroacetyl chloride (2.83 ml, 35.34 mmol). The reaction mixture was stirred at 0° C. for 0.5 h and at room temperature for 3 h. Then solvent was evaporated, the crude mixture was dissolved in EtOAc (100 ml) and poured into 200 ml of H₂O. The organic layer was separated, the water layer was extracted with EtOAc, the combined organic extract was washed with H₂O, brine, dried over MgSO₄, and the solvent was removed. The crude compound was dissolved in 30 ml of EtOAc, hexane (150 ml) was added and cooled to 0° C. to precipitate the brown solid. The solid was filtered and dried to afford 4.9 g of 11 in 67% yield.¹H NMR (CDCl₃, 400 MHz): δ2.82 (t, 2H, J=6.8 Hz), 3.54 (q, 2H, J=6.4 Hz), 4.02 (s, 2H), 6.55-6.65 (bs, 1H), 7.12-7.15 (m, 2H), 7.26-7.30 (m,2H).

References:

US2007/293475,2007,A1 Location in patent:Page/Page column 4