1-Hydroxybenzotriazole → N-{2-oxo-2-[4-(2-trifluoromethyl-phenylamino)-piperidin-1-yl]-ethyl}-4-phenylamino-benzamide

Participants

Reaction Steps

To a stirred solution of (4-phenylamino-benzoylamino)-acetic acid (0.058 g, 0.00021 mol) in DMF (5 mL) was added DIPEA (0.069 g, 0.00054 mol), HOBt (0.028 g, 0.0002142 mol) and EDCI.HCl (0.085 g, 0.00045 mol) at ambient temperature. After 2 minutes piperidin-4-yl-(2-trifluoromethyl-phenyl)-amine dihydrochloride (0.050 g, 0.00019 mol) was added and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water and the product was extracted with ethyl acetate. The ethyl acetate layer was collected, washed with brine solution, dried over sodium sulfate and concentrated under reduced. The resulting residue was purified by column chromatography using silica gel 60-120 mesh (60% ethyl acetate in hexane) to afford 0.06 g (68%) of N-{2-oxo-2-[4-(2-trifluoromethyl-phenylamino)-piperidin-1-yl]-ethyl}-4-phenylamino-benzamide. LCMS: 497.21 (M+1)+, 95.3%, 1H NMR (DMSO-d6): δ 8.6 (s, 1H), 8.2 (t, 1H), 7.8 (d, 2H), 7.4 (m, 4H), 7.2 (d, 2H), 7.1 (m, 3H), 6.9 (t, 1H), 6.7 (t, 1H), 4.7 (d, 1H), 4.3 (d, 1H), 4.1 (s, 2H), 3.9 (d, 1H), 3.7 (s, 1H), 2.8 (t, 1H), 2.0 (t, 2H), 1.5 (m, 2H).

Provenance & Evidence