Acetic Acid → HCID 86649245, compound

Participants

Reaction Conditions

Reaction Steps

In a 2-5 mL Emrys™ process vial, the ethyl 1-formyl-4-oxo-4H-quinolizine-3-carboxylate (599 mg, 2.44 mmol) and the 4-[4-(trifluoromethyl)phenyl]piperidinium chloride (672 mg, 2.53 mmol) were diluted with 4.9 mL of dichloroethane, which was neutralized with the addition of triethylamine (0.41 mL, 2.93 mmol). To the stirring mixture was added glacial acetic acid (0.84 mL, 14.7 mmol) and resin-bound MP-cyanoborohydride (307 mg, 4.89 mmol). The mixture was heated via Emrys Optimizer™ microwave to 120° C. for 20 minutes. After filtration, the filtrate was washed with water (3×20). The organic layer was dried over sodium sulfate, filtered, concentrated, and purified by silica gel chromatography eluting with 30-80% EtOAc in hexanes to provide ethyl 4-oxo-1-({4-[4-(trifluoromethyl)phenyl]piperidin-1-yl}methyl)-4H-quinolizine-3-carboxylate.

Provenance & Evidence