Hydrochloric Acid → HCID 178437831, compound

Participants

Reaction Steps

3-Nitro-9-phenylnonan-4-one (0.050 g, 0.19 mmol) reacted with concentrated HCl (0.95 mmol) and palladium, 5 wt. % on activated carbon (0.081 g, 0.038 mmol) under H2, then reacted with cyanamide (0.040 g, 0.95 mmol) according to the general procedure. Purification by column chromatography gave 0.014 g (29%) over two steps as a yellow oil: 1H NMR (300 MHz, CD3OD) δ 7.25 (m, 2H), 7.14 (m, 3H), 2.59 (t, J=7.5 Hz, 2H), 2.42 (m, 4H), 1.63 (m, 4H), 1.28 (m, 2H), 1.13 (t, J=7.5 Hz, 3H) ppm; 13C NMR (75 MHz, CD3OD) δ 146.2, 142.4, 128.2, 128.1, 125.5, 123.6, 121.3, 35.5, 31.1, 28.7, 28.1, 22.9, 16.5, 13.1 ppm; IR νmax (cm−1) 3327, 2934, 1680, 1453, 1016, 749; HRMS (FAB) calcd for C16H23N3 (MH+) 258.1965, found 258.1973.

Provenance & Evidence