N-methyl-2-pyrrolidone → 4-[3-(Hydroxymethyl)-8-methylquinolin-2-yl]piperazin-2-one

Participants

Reaction Conditions

Reaction Steps

(2-Chloro-8-methylquinolin-3-yl)methanol (250 mg, 1.13 mmol), 2-oxopiperazine (566 mg, 5.66 mmol), DIPEA (1 mL, 5.66 mmol) and NMP (3 mL) were combined in a sealed tube and heated to 140° C. for 24 h. After cooling, the reaction mixture was dissolved in a 1:1 mixture of EtOAc and Et2O (100 mL) and washed with saturated brine (3×25 mL). The organic layer was dried (MgSO4) and concentrated in vacuo. Purification by column chromatography on silica, eluting with 5% MeOH in DCM, afforded the title compound (155 mg, 51%) as a white solid. LCMS (ES+) 272 (M+H)+.

Provenance & Evidence