Ethyl Bromide → HCID 18705851, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-(dipropylamino)-6,7-dihydrocyclopent[f]isoindole-1,3(2H,5H)-dione (93, 0.15 g, 0.52 mmol) in DMF (10 mL) at 0° C. was added anhydrous K2CO3 (0.14 g, 1.04 mmol) followed by ethyl bromide (0.06 mL, 0.79 mmol). The reaction was stirred at 0° C. for 2 hr then allowed to warm to r.t. Continued stirring overnight then quenched with H2O. The solution was extracted with CH2Cl2 and the organic layers were washed with brine, dried (MgSO4), and concentrated. The residue was further concentrated on the high vac to remove any excess DMF and the resulting greenish solid was purified using silica gel, eluting with 3:1 hexane/acetone to give 95 as an off-white solid. The solid was converted to an HCl salt and recrystallized from hot MeOH/EtOAc to give 95 as a white solid (m.p. 225-230° C.).

Provenance & Evidence