Pyridine → HCID 24872412, compound

Participants

Reaction Steps

2-Acetoxy-5-chlorobenzoic acid (0.257 g, 1.20 mmol), phosphorus oxychloride (0.184 g, 1.20 mmol) and pyridine (0.095 g, 1.20 mmol) were added to a solution of 1-[4-(4-amino-2-fluorophenyl)piperazin-1-yl]ethanone (compound of Reference Example 85; 0.237 g, 1.00 mmol) in tetrahydrofuran (3 ml) under ice cooling, and the mixture was stirred under ice cooling for 3 hours. The reaction mixture was neutralized by addition of saturated aqueous sodium hydrogencarbonate, diluted with water, and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. 6N Hydrochloric acid (6 ml) was added to the residue obtained by evaporation of the solvent under reduced pressure, and the mixture was refluxed for 5 hours. The reaction mixture was cooled to room temperature and neutralized by addition of 2N aqueous sodium hydroxide. The precipitated solid was collected by filtration, washed with water, and purified by column chromatography on silica gel (methanol:chloroform=1:10) to give the title compound (0.017 g, 5%) as a yellow solid.

Provenance & Evidence