3,5-Bis(trifluoromethyl)benzoic acid → N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methyl-3,5-bis(trifluoromethyl)benzamide

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Reaction Steps

[(2S)-2-(4-Fluorophenyl)pent-4-en-1-yl]methylamine (Bioorg. Med. Chem. Lett; 2001; 265-270; 300 mg, 1.55 mmol) was dissolved in DMF (3 mL) and to the resultant solution were added 3,5-bis(trifluoromethyl)benzoic acid (440 mg, 1.71 mmol), TBTU (548 mg, 1.71 mmol) and DIPEA (803 mg, 6.21 mmol) in the given order. The mixture was stirred for 2 h at room temperature, diluted with an aqueous solution of NaHCO3 (saturated, 25 mL) and then extracted three times with ethyl acetate. The combined organic solutions were washed three times with water and then dried over Na2SO4. The solvent was removed by evaporation and the residue was chromatographed on silica gel using a mixture of heptane and ethyl acetate as eluent (4:1). There was obtained 576 mg (85%) of N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methyl-3,5-bis(trifluoromethyl)benzamide as an oil. 1H NMR (400 MHz, CDCl3): 2.2-2.4 (cm, 2H), 2.7 (s, 2H), 2.9-3.9 (cm, 4H), 4.9-5.1 (m, 2H), 5.4-5.8 (m, 1H), 6.8-7.1 (cm, 3H), 7.2-7.5 (3H), 7.9 (s, 1H); LCMS: m/z 434 (M+1)+.

Provenance & Evidence