Sodium Iodide → 7-chloro-3-(3,5-dimethylphenyl)-4-(1-methyl-piperidin-3-ylmethoxy)-1H-quinolin-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 7-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-1H-quinolin-2-one (100 mg in 3 mL dry N,N-dimethylformamide) was added 68 mg 3-chloromethyl-1-methylpiperidine hydrochloride followed by 55 mg sodium iodide and 97 mg potassium carbonate and the mixture heated to 80° C. on an oil bath. After 7 hours, an additional portion of potassium carbonate (48 mg) and 3-chloromethyl-1-methylpiperidine hydrochloride (68 mg) were added and the reaction allowed to proceed at 80° C. for another 14 hours. At this time the reaction was cooled to room temperature and quenched by pouring into 25 mL of ice/water. The precipitate was collected by filtration and washed with cold water. Purification of the crude by flash chromatography on silica gel (chloroform: 10% ammonium hydroxide in methanol, 95:5) provided the title compound (53 mg). MASS=411 (M+H)

Provenance & Evidence