Reaction #2612

Reaction equation

boron tribromide

4-Acetylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide

sodium bicarbonate

→

title compound

Yield 76.7%

4-Acetylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-hydroxyphenyl)benzamide

Yield 76.7%

Solvents

methylene chloride

methylene chloride

Conditions

Workup

1. 1
   Extractionextracted with ethyl acetate
2. 2
   WashThe resulting organic layer was washed with saturated sodium bicarbonate aqueous solution and saturated brine
3. 3
   Dryingdried on anhydrous sodium sulfate
4. 4
   workup.DISTILLATIONThereafter, the solvent was distilled off under a reduced pressure
5. 5
   Otherthe resulting residue was purified by a silica gel column chromatography (ethyl acetate-chloroform:methanol=10:1)

Procedure

4-Acetylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (50.0 mg, 0.10 mmol) was dissolved in methylene chloride (3.0 ml) to which was subsequently added a methylene chloride solution (1 ml) of boron tribromide (0.018 ml, 0.19 mmol) at 0° C. After 12 hours of stirring at 0° C. to room temperature, the reaction solution was mixed with saturated sodium bicarbonate aqueous solution and extracted with ethyl acetate. The resulting organic layer was washed with saturated sodium bicarbonate aqueous solution and saturated brine, and dried on anhydrous sodium sulfate. Thereafter, the solvent was distilled off under a reduced pressure, and the resulting residue was purified by a silica gel column chromatography (ethyl acetate-chloroform:methanol=10:1) to obtain 37.3 mg (76.7%) of the title compound in a light yellow amorphous form.

Source