Hydrochloric Acid → HCID 18679314, compound

Participants

Reaction Steps

A solution containing 10-benzyl-7-methyl-7,8,9,10,11,12-hexahydro-3H-azepino[4,5-b]pyrano[3,2-e]indole (0.18 g., 0.51 mmol, Example 1) in ethanol (20.0 mL) was hydrogenated in the presence of palladium-on-carbon (0.07 g.) and 2 N hydrochloric acid (0.51 mL, 0.51 mmol) at 50 psi for 48 hours. After filtration through a pad of celite, the filtrate was concentrated in vacuo. The residue was recrystalized from EtOAc/MeOH to yield the title compound (0.13 g, 84%) as a light yellow solid. M.p.>217° C. (dec.); IR (KBr) 2946, 2877, 2844, 2809, 1609, 1585, 1551, 1467, 1447, 1280, 1267, 1255, 1238, 1109, 787 cm−1; 1H NMR (300 MHz, DMSO-d6) δ 7.07, 6.52, 4.04-4.01, 3.57, 3.31-3.28, 3.19-3.12, 3.07-3.03, 1.96-1.92; 13C NMR (DMSO-d6) δ 148.5, 136.8, 131.2, 125.2, 112.3, 112.1, 110.9, 108.8, 65.4, 46.3, 44.2, 29.7, 23.1, 22.6, 22.4; MS (ESI+) m/z 257 (M++H); HRMS cacld for C16H20N2O+H: 257.1654, found: 257.1646; Anal. Calcd. for C16H20N2O.HCl.H2O: C, 61.83; H, 7.46; N, 9.01. Found: C, 62.07; H, 7.41; N, 9.01.

Provenance & Evidence