Cyclohexanecarbonyl chloride → N-(1-benzyl-3-methylpyrrolidin-3-yl)-N-[(1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)methyl]cyclohexanecarboxamide

Participants

Reaction Steps

To 3-{[(1-benzyl-3-methylpyrrolidin-3-yl)amino]methyl}-1-methylquinolin-2(1H)-one (1846 mg, 5.11 mmol) in CH2Cl2 (25 ml) was added DIEA (1.338 ml, 7.66 mmol). Cyclohexane carbonyl chloride (0.757 ml, 5.62 mmol) was added and the reaction stirred for 2 hours. The reaction was quenched with MeOH then concentrated in vacuo. The resulting material was twice purified by silica gel chromatography on an Isco Companion (5-35% acetone/hexane for first run, 5-25% acetone/hexane for second run). 2.12 g, 88% over two steps.

Provenance & Evidence