m-Anisoyl chloride → 3-methoxy-N-{1-[(2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)methyl]piperidin-4-yl}benzamide

Participants

Reaction Steps

To a CHCl3 (5.00 mL) solution of the compound (250 mg) obtained in Step 1-6, iPr2NEt (370 μL) and 3-methoxybenzoyl chloride (180 mg) were added and the mixture was stirred at room temperature for three days. To the reaction mixture, a saturated aqueous NaHCO3 solution was added and the solution was extracted with CHCl3 four times. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography [(silica gel 60 N, mobile phase: MeOH/CHCl3=0/100 to 10/90; v/v) and (Chromatorex NH, mobile phase: CHCl3) in this order] to obtain a solid. To the solid obtained, IPA was added at room temperature and the mixture was stirred for one hour, filtrated and washed with IPA and hexane to obtain the titled compound (159 mg, a colorless solid).

Provenance & Evidence