Hydrochloric Acid → HCID 9817950, compound

Participants

Reaction Steps

A solution of 5-benzyloxy-3-(2-dimethylamino-ethyl)-1H-indole-1-carboxylic acid tert-butyl ester (303 mg, 0.77 mmol) and 4N hydrochloric acid (192 ml, 0.77 mmol) in ethanol (10 ml) was hydrogenated over 10% palladium on carbon (100 mg) at 40 psi for 4 hours. The catalyst was removed by filtration. The filtrate was evaporated and the residue was partitioned between aqueous sodium hydrogen carbonate and dichloromethane. 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/aqueous ammonia (60:8:1) to give the title compound (117 mg, 50%) as a colourless solid. δH (360 MHz, CDCl3) 1.64 (9H, s), 2.45 (6H, s), 2.73-2.80 (2H, m), 2.88-2.93 (2H, m), 6.82-6.85 (1H, m), 6.96 (1H, br s), 7.33 (1H, br s), 7.92 (1H, m). m/z (CI+) 305 [MH]+. Found: C, 64.07; H, 8.07; N, 8.71. C17H24N2O3. 0.8 H2O requires C, 64.01; H, 8.15; N, 8.78%.

Provenance & Evidence