反应详情

7-Nitro-1-phenylundecan-6-one (0.049 g, 0.17 mmol) reacted with concentrated HCl (0.85 mmol) and palladium, 5 wt. % on activated carbon (0.072 g, 0.034 mmol) under H2, then reacted with cyanamide (0.035 g, 0.84 mmol) according to the general procedure. Purification by column chromatography gave 0.025 g (52%) over two steps as a yellow oil: 1H NMR (400 MHz, CD3OD) δ 7.22 (m, 2H), 7.15 (m, 3H), 2.60 (t, J=7.2 Hz, 2H), 2.43 (m, 4H), 1.64 (m, 6H), 1.34 (m, 4H), 0.94 (t, J=7.6 Hz, 3H) ppm; 13C NMR (75 MHz, CD3OD) δ 146.4, 142.4, 128.2, 128.1, 125.6, 122.1, 121.9, 35.5, 31.2, 31.1, 28.7, 28.2, 23.0, 22.8, 21.9, 12.9 ppm; IR νmax (cm−1) 3166, 2930, 2857, 1680, 1453, 1030, 748, 699; HRMS (FAB) calcd for C18H27N3 (MH+) 286.2278, found 286.2288.

1. customPurification by column chromatography
2. customgave 0.025 g (52%) over two steps as a yellow oil