2-(Trifluoromethyl)benzoic acid → HCID 17683255, compound

Participants

Reaction Conditions

Reaction Steps

HOBt (4.26 g, 31.5 mmol) and DIEA (10.19 g, 78.89 mmol) were added to a stirred solution of 2-trifluoromethylbenzoic acid (5 g, 26.3 mmol) in DMF (20 mL). The reaction mixture was cooled to 10° C. and EDCI.HCl (12.6 g, 65.7 mmol) followed by 1-benzyl-piperazine (5.56 g, 31.55 mmol) were then added. The reaction mixture was stirred at room temperature overnight, then diluted with water and the product extracted with ethyl acetate. The ethyl acetate was washed with brine solution, dried over Na2SO4 and evaporated. The resulting residue was purified by column chromatography using silica gel 60-120 mesh with (30% ethyl acetate in hexane) to afford 8.6 g (93%) of (4-benzyl-piperazin-1-yl)-(2-trifluoromethyl-phenyl)-methanone. 1H NMR: (DMSO-d6): δ 7.8 (m, 2H), 7.6 (t, 1H), 7.4 (d, 1H), 7.3 (m, 5H), 3.6 (m, 2H), 3.5 (s, 2H), 3.1 (m, 2H), 2.4 (m, 1H), 2.3 (m, 2H), 2.2 (m, 1H).

Provenance & Evidence