HCID 66965003, compound → 1H-1-Benzazepine

Participants

Reaction Steps

To a solution of the dihydrobenzazepine (0.20 g, 0.49 mmol) from step I above in ethanol (30 mL) was added palladium(II) hydroxide (0.20 g, 0.28 mmol). The reaction solution was shaken under hydrogen (35 psi) for 1 h. The resultant reaction mixture was filtered through a pad of Celite and concentrated in vacuo. The crude product was purified by preparative HPLC to give the desired racemic benzazepine (85 mg, 42%) as an off-white foam: 1H NMR (CDCl3, 500 MHz) δ 8.33 (d, J=5.0 Hz, 2H), 7.15 (d, J=8.0 Hz, 2H), 7.06 (d, J=8.0 Hz, 2H), 6.81 (d, J=2.5 Hz, 1H), 6.65 (d, J=7.5 Hz, 1H), 6.62-6.53 (br, 1H), 6.51 (t, J=5.0 Hz, 1H), 4.21 (d, J=9.0 Hz, 1H), 3.96 (t, J=5.0 Hz, 4H), 3.89 (br d, J=12.5 Hz, 1H), 3.70 (d, J=14.0 Hz, 1H), 3.20 (t, J=5.5 Hz, 4H), 3.15-3.08 (br, 1H), 2.93 (t, J=10.5 Hz, 1H), 2.36 (s, 3H), 2.35 (s, 3H), 2.32-2.25 (m, 1H), 2.12-2.04 (br, 1H); ESI MS m/z 414 [M+H]+.

Provenance & Evidence