Hydrochloric Acid → HCID 10292950, compound

Participants

Reaction Steps

A mixture of 3-benzoyl-9-(phenylsulfonyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (Step III, 1.25 g, 2.81 mmol) and potassium hydroxide (1.58 g, 28.1 mmol) in ethylene glycol (30 mL) is heated at 130° under nitrogen for 92 hr. Upon cooling, the mixture is diluted with H2O and extracted into ethyl acetate (3 x). The combined extracts are washed with H2O (2 x) and saline, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to give a solid. The solid is dissolved in hot methylene chloride/methanol and treated with methanolic hydrochloric acid. The resultant mixture is concentrated and crystallized from ethyl acetate/methanol to give the title compound, mp>300°; IR (drift) 2820, 2792, 2747, 2717, 2704, 2665, 2651, 1299, 1147, 1096, 803, 729, 687, 643 and 621 cm−1; NMR (300 MHz, DMSO-d6) 9.41, 8.13, 7.85-7.95, 7.50-7.65, 3.70 and 3.10-3.40 δ; MS (EI) m/z 340 (M+), 298, 157, 156, 128, 78, 74, 73, 58 and 57; HRMS (FAB) calculated for C19H21N2O2S=341.1324, found=341.1319.

Provenance & Evidence