反应详情

7-Nitro-1-phenyldodecan-6-one (0.090 g, 0.29 mmol) reacted with concentrated HCl (1.45 mmol) and palladium, 5 wt. % on activated carbon (0.125 g, 0.060 mmol) under H2, then reacted with cyanamide (0.062 g, 1.47 mmol) according to the general procedure. Purification by column chromatography gave 0.071 g (81%) over two steps as a yellow oil: 1H NMR (300 MHz, CD3OD) δ 7.20 (m, 2H), 7.14 (m, 3H), 2.59 (t, J=7.5 Hz, 2H), 2.42 (m, 4H), 1.56 (m, 6H), 1.32 (m, 6H), 0.90 (t, J=7.2 Hz, 3H) ppm; 13C NMR (75 MHz, CD3OD) δ 146.3, 142.5, 128.3, 128.1, 125.6, 122.1, 121.8, 35.5, 31.1, 31.1, 28.7, 28.7, 28.2, 23.1, 23.0, 22.3, 13.3 ppm; IR νmax (cm−1) 3169, 2928, 2857, 1680, 1453, 1202, 1030, 746, 699; HRMS (FAB) calcd for C19H29N3 (MH+) 300.2434, found 300.2441.

1. customPurification by column chromatography
2. customgave 0.071 g (81%) over two steps as a yellow oil