Reaction #2609

Reaction equation

ammonium chloride

sodium hydride

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

methyl iodide

→

title compound

Yield 80.4%

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

Yield 80.4%

Solvents

THF

Conditions

Workup

1. 1
   Otherat room temperature
2. 2
   Extractionextracted with ethyl acetate
3. 3
   WashThe resulting organic layer was washed with water and saturated brine
4. 4
   Dryingdried on anhydrous sodium sulfate
5. 5
   OtherThereafter, the solvent was removed by evaporation
6. 6
   Otherthe resulting residue was recrystallized from methanol-ether

Procedure

4-Acetylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(4-methoxyphenyl)benzamide (155.0 mg, 0.30 mmol) was dissolved in THF (3.0 ml) to which were subsequently added 60% sodium hydride {28.0 mg, 0.70 mmol) and methyl iodide (0.060 ml, 1.00 mmol) at room temperature, followed by 2 hours of stirring. The reaction solution was mixed with saturated ammonium chloride aqueous solution and extracted with ethyl acetate. The resulting organic layer was washed with water and saturated brine, and dried on anhydrous sodium sulfate. Thereafter, the solvent was removed by evaporation, and the resulting residue was recrystallized from methanol-ether to obtain 128.0 mg (80.4%) of the title compound in a colorless powder form.

Source