Pentylamine → 5-[4-(2-Trifluoromethylbenzoyl)piperazin-1-YL]-[1,3,4]oxadiazole-2-carboxylic acid pentylamide

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5-[4-(2-Trifluoromethylbenzoyl)piperazin-1-yl]-[1,3,4]oxadiazole-2-carboxylic acid ethyl ester (0.050 g, 0.126 mmol) was added to the mixture of n-pentylamine (1 mL) and sodium cyanide (0.012 g, 0.251 mmol). The reaction mixture was stirred at room temperature over night. The mixture was evaporated to dryness, then diluted with 5 mL of water and extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4, and then concentrated. The title compound was obtained in 86% yield (0.047 g) after column purification. 1H NMR (300 MHz, CDCl3) δ 7.74-7.71 (m, 1H), 7.64-7.52 (m, 2H), 7.33-7.31 (m, 1H), 6.91 (t, J=5.4 Hz, 1H), 4.09-3.98 (m, 1H), 3.87-3.6 (m, 3H), 3.58-3.45 (m, 2H), 3.42-3.36 (m, 2H), 3.30-3.27 (m, 2H), 1.63-1.5 (m, 2H), 1.33-1.29 (m, 4H), 0.87 (t, J=6.6 Hz, 3H). 13C NMR (75 MHz, CDCl3) δ 167.6, 164.6, 153.9, 153.5, 133.9, 132.4, 129.6, 128.97, 127.1, 126.9, 126.8, 126.7, 125.4, 121.8, 46.0, 45.7, 45.6, 40.8, 39.7, 29.0, 28.9, 22.3, 13.9. MS (ES+) m/z 440 (M+1).

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