Ethanol → HCID 14031281, compound

Participants

Reaction Steps

A solution of 14.0 g (0.08 mole) of cyclopent[b]indolone of Example 8, 9.96 g (0.12 mole) of dimethylamine hydrochloride and 7.2 g (0.24 mole) of paraformaldehyde in 280 mL of 2B ethanol was heated to reflux and stirred mechanically for 20 hours. The solvent was removed on a rotary evaporator at 35° C. The residue showed unreacted cyclopent[b]indolone of Example 8, the desired title compound and a third component, identified as an ethoxymethyl substituted compound by thin layer chromatography. The residue was chromatographed on silica gel (dry column) eluting with the lower phase of a mixture prepared by shaking 90 parts CHCl3, 30 parts CH3OH, 10 parts H2O, and 6 parts acetic acid. Fractions containing starting the ketone and the ethoxymethyl substituted compound eluted first. The fractions containing the title compound were washed with 10% NH4OH, dried over Na2SO4, and concentrated on a rotary evaporator to give 6.7 g (36%) of title compound as an off-white solid. A sample, recrystallized from ethanol, had mp 165°-166° C.

Provenance & Evidence