Sodium Bicarbonate → HCID 19927832, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1,2,3,4-tetrahydro-6-methoxy-2-[[1-(phenylmethyl)-4-piperidinyl]methyl]cyclopent[b]indol-3-one (200 mg, 0.51 mmol) and 48% HBr (30 ml) was heated to 110° C. for 3.5 hours. The reaction mixture was allowed to cool and saturated sodium bicarbonate was added until pH 8. The mixture obtained was filtered and the aqueous filrate was extracted with ethanol and the resulting mixture was filtered. Aqueous Na2S2O4 was added to the ethanolic filtrate and the light brown solution obtained was concentrated. The residue was partitioned between water and boiling ethyl acetate. The organic layer was combined and washed with water, brine, dried, filtered and concentrated. The residue was purified through silica gel column chromatography to give the title compound as a yellow solid (100 mg). The material was recrystallized from ethanol to give a pale yellow solid, mp. 250°-252° C.; Anal. Calc. for C24H26N2O2.0.25H2O: C, 76.06; H, 7.05; N, 7.39; ound: C, 76.27; H, 6.67; N, 7.36.

Provenance & Evidence