Acetic Acid → HCID 23283210, compound

Participants

Reaction Steps

The organic layer was separated and the solvent evaporated. The crude product was purified by column chromatography on silica using dichloromethane/methanol/ammonia (40:8:1) to give 2-[5-(1,2,4-triazol-4-yl)-1H-indol-3-yl]ethylamine as a brown oil (1.9 g, 49%). This tryptamine (1.0 g, 4.4 mmol), 1-benzylpiperidin-4-one (874 mg, 4.6 mmol), glacial acetic acid (1.58 g, 26.4 mmol) and sodium cyanoborohydride (290 mg, 4.6 mmol) were stirred in methanol (75 ml) at room temperature for 18 hours. The mixture was treated with 2M sodium hydroxide (to pH=8), evaporated and the aqueous partitioned between 2M sodium hydroxide (30 ml) and ethyl acetate (50 ml). The organic layer was separated and the aqueous re-extracted with ethyl acetate (2×50 ml). The combined organics were washed with saturated sodium chloride solution (2×30 ml), dried (sodium sulphate) and evaporated. The crude product was purified by column chromatography on silica using dichloromethane/methanol/ammonia (10:1:0.1) to afford the title compound free base as a solid (1.4 g, 79%). The hydrogen oxalate salt had mp 187-189° C., MS, ES+, m/z=401 for (M+H)+. (Found: C, 56.11; H, 5.88; N, 14.08. C24H28N6. 2C2H2O4. H2O requires C, 56.18; H, 5.72; N, 14.04%).

Provenance & Evidence