Hydrochloric Acid → HCID 20094419, compound

Participants

Reaction Steps

6-[(2,3-Dihydro-1,4-benzodioxin-2-yl)methylamino]-N-[4-(trifluoromethyl)phenyl]hexanamide monohydrochloride (201 mg), 37% aqueous formaldehyde (0.18 mL) and sodium cyanoborohydride (38 mg) were stirred in methanol (4.8 mL) for 96 hours at 20°-25° C. under nitrogen atmosphere. Saturated sodium bicarbonate (20 mL) was added to the reaction and extracted with dichloromethane (2×20 mL). The combined extracts were dried (Na2SO4) and concentrated in vacuo. The resulting oil was chromatographed eluting with ethyl acetate and 10:90 ethanol:ethyl acetate to give a white solid (Rf of 0.52 in 10:90 ethanol:ethyl acetate) which was dissolved in ethanol and treated with 1.0M aqueous HCl (1 ml). The solution was concentrated in vacuo to give an oil which was dissolved in 70:30 ethyl acetate:hexane and concentrated. A hygroscopic white solid (151 mg) remained.

Provenance & Evidence