Acetic Acid → HCID 86653282, compound

Participants

Reaction Steps

A mixture of the ethyl 1-formyl-4-oxo-4H-quinolizine-3-carboxylate (0.891 g, 3.63 mmol), 4-piperazin-1-ylbenzonitrile (0.952 g, 5.09 mmol), glacial acetic acid (1.25 mL, 21.8 mmol) and 18.2 mL of dichloroethane was stirred vigorously. To the stirring mixture was added sodium triacetoxyborohydride (1.08 g, 5.09 mmol), which was stirred for 18 hours. The mixture was quenched with a 10% sodium carbonate solution, extracted with dichloromethane (1×40 mL), and partitioned between water and dichloromethane. The organic layer was dried over sodium sulfate, filtered, concentrated, and purified by silica gel chromatography eluting with EtOAc to yield ethyl 1-{[4-(4-cyanophenyl)piperazin-1-yl]methyl}-4-oxo-4H-quinolizine-3-carboxylate.

Provenance & Evidence