Triethylamine → 4-(3-methyl-5-(5-(trifluoromethyl)pyridin-2-yloxy)benzylidene)-N-(pyridin-3-yl)piperidine-1-carboxamide

Participants

Reaction Steps

To a solution of 2-(3-methyl-5-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine (445 mg, 1.276 mmol) in DMSO (3 mL) was added phenyl pyridin-3-ylcarbamate (273 mg, 1.276 mmol) followed by triethylamine (0.53 mL, 3.83 mmol). The resulting mixture was stirred at RT for 12 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic extract was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (30% acetone-70% hexane) to give the pure title compound (0.350 g, 58% yield). 1H NMR (500 MHz, CDCl3): δ 8.45 (m, 2H), 8.27 (s, 1H), 8.01 (m, 1H), 7.90 (m, 1H), 7.02 (m, 1H), 6.92 (s, 1H), 6.84 (d, J=20 Hz, 2H), 6.47 (s, 1H), 6.38 (s, 1H), 3.16 (s, 2H), 3.52 (s, 2H), 2.61 (s, 2H), 2.47 (s, 2H), 2.37 (s, 3H); 13C NMR (125 MHz, CDCl3): δ 165.87, 154.81, 153.01, 145.50, 143.77, 141.29, 139.84, 138.79, 137.99, 136.71, 127.58, 126.93, 124.77, 123.58, 122.62, 121.62, 120.13, 118.82, 111.38, 45.72, 44.70, 35.78, 29.20, 21.45; m/z (469.5, M+H+); HPLC: 98.5%.

Provenance & Evidence