Water → N-{2-Oxo-2-[4-(2-trifluoromethyl-benzyl)-piperazin-1-yl]-ethyl}-4-phenoxy-benzamide

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Reaction Conditions

Reaction Steps

K2CO3 (130 mg, 0.95 mmol) was added to N-(2-Oxo-2-piperazin-1-yl-ethyl)-4-phenoxy-benzamide hydrochloride (141 mg, 0.38 mmol) in 5 mL of DMF. After 10 minutes atr room temperature, 1-Bromomethyl-2-trifluoromethyl-benzene (75 mg, 0.32 mmol) was added and the resulting mixture was stirred at 60° C. for 4 hours. Water was then added, and the product was extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulphate and concentrated. Purification by column chromatography (60-120 mesh silica gel using 6:4 EtOAc and Hexane as the eluent) afforded N-{2-Oxo-2-[4-(2-trifluoromethyl-benzyl)-piperazin-1-yl]-ethyl}-4-phenoxy-benzamide in 39% yield. LC-MS purity: 86%. 1H NMR (DMSO-D6): δ 8.5 (t, 1H), 7.9 (d, 2H), 7.8 (d, 1H), 7.7 (q, 2H), 7.4 (m, 3H), 7.2 (t, 1H), 7.1 (m, 2H), 7 (m, 2H), 4.1 (d, 2H), 3.7 (s, 2H), 3.5 (m, 4H), 2.4 (m, 4H).

Provenance & Evidence