Hydrochloric Acid → HCID 131717788, compound

Participants

Reaction Conditions

Reaction Steps

Serotonin hydrochloride hemihydrate (200 mg) and N-[4-(trifluoromethyl)phenyl]-5-oxo-hexanamide (246 mg) were stirred under nitrogen in methanol (8 mL) and treated with sodium cyanoborohydride (85 mg). After stirring 66 hours at 23° C., sodium bicarbonate (250 mg) and water (5 mL) were added. Thirty minutes later, the reaction was diluted with water (50 mL) and extracted with 1:4 2-propanol:dichloromethane (40 mL, 40 mL, 20 mL) and the extracts dried (Na2SO4) and concentrated in vacuo to an oil. The oil was chromatographed with 5:10:90, then 3:50:50 triethylamine:ethanol:ethyl acetate to isolate a component with Rf of 0.15 (5:10:90 triethylamine:ethanol:ethyl acetate). This oil was dissolved in ethanol (50 mL), treated with 1:9 concentrated hydrochloric acid:ethanol (2 mL), and concentrated in vacuo. Reconcentration from ethanol (50 mL) and placing under vacuum gave the title compound as an off-white solid (272 mg).

Provenance & Evidence