Hydrochloric Acid → HCID 22396825, compound

Participants

Reaction Steps

A solution of 3-benzyl-9-phenoxy-1,2,3,4,5,6-hexahydro-azepino[4,5-b]indole (0.092 g, 0.26 mmol) in ethanol (20.0 mL) was hydrogenated in the presence of palladium on carbon (0.04 g) and 2 N hydrochloric acid (0.13 mL, 0.26 mmol,) at 50 psi for 16 h. After filtration through a pad of Celite, the filtrate was concentratec in vacuo to dryness. The residue was recrystalized from EtOAc/MeOH to give 0.071 g (99%) of colorless solid as the desired product: mp>227° C. (dec.); 1H NMR (400 MHz, DMSO-d6) δ 11.10, 9.60, 7.32-7.28, 7.11, 7.01, 6.88, 6.77, 3.36-3.27, 3.21-3.19, 3.05-3.01; 13C NMR (100.6 MHz, DMSO-d6) δ 159.1, 148.5, 136.4, 131.5, 129.6, 128.5, 121.7, 116.6, 114.0, 111.8, 109.7, 108.1, 46.6, 44.8, 24.7, 20.8; MS (EI) m/z 278 (M+); HRMS cacld for C18H18N2O+H: 279.1497, found: 279.1508; Anal. Calcd. for C18H18N2O.HCl: C, 68.67; H, 6.08; N, 8.90. Found: C, 67.95; H, 6.14; N, 8.99.

Provenance & Evidence