Hydrochloric Acid → HCID 9796627, compound

Participants

Reaction Steps

A solution of [5-benzyloxy-3-(2-dimethylamino-ethyl)-1H-indol-1yl]phenylmethanone (300 mg, 0.75 mmol) and 4N hydrochloric acid (190 ml, 0.76 mmol) in ethanol (10 ml) was hydrogenated over 10% palladium on carbon (100 mg) at 35 psi for 3 hours. The catalyst was removed by filtration. The filtrate was evaporated, and the residue was partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate. The aqueous was further extracted with dichloromethane (×2). The combined extracts were dried (K2CO3), filtered and evaporated. The residue was purified by chromatography on silica gel, eluting with dichloromethane/methanol/aqueotus ammonia (80:8:1) to give the title compound (120 mg, 52%), as a colourless solid; mp 154°-156° C. δH (360 MHz, CDCl3) 2.40 (6H, s), 2.70-2.75 (2H, m), 2.83-2.88 (2H, m), 6.86-6.90 (2H, m), 7.04 (1H, s), 7.49-7.61 (3H, m), 7.68-7.71 (2H, m), 8.17 (0.5H, s), 8.20 (0.5H, s). m/z (CI+) 309 [MH]+. Found: C, 73.22; H, 6.48; N, 8.74. C19H20N2O2.0.2 H2O requires C, 73.15; H, 6.59; N, 8.98%.

Provenance & Evidence