Reaction #2564

Reaction equation

sodium hydride

4-methoxymethyl-N-(2-methoxyphenyl)benzamide

1-(2-chloroethyl)-4-(4-fluorobenzoyl)piperidine hydrochloride

sodium iodide

→

title compound

Yield 54.7%

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

Yield 54.7%

Solvents

DMF

Conditions

Workup

1. 1
   Otherat room temperature
2. 2
   workup.WAITat 60° C. for 3.5 hours
3. 3
   OtherDMF was removed by evaporation
4. 4
   workup.ADDITIONThe resulting residue was diluted with water (10 ml)
5. 5
   Extractionextracted with ethyl acetate
6. 6
   Washthe organic layer was washed with water and saturated brine
7. 7
   Dryingdried on anhydrous sodium carbonate
8. 8
   OtherThereafter, the solvent was removed by evaporation
9. 9
   Otherthe resulting residue was purified

Procedure

In an atmosphere of argon, 4-methoxymethyl-N-(2-methoxyphenyl)benzamide (126 mg, 0.464 mmol), 1-(2-chloroethyl)-4-(4-fluorobenzoyl)piperidine hydrochloride (157 mg, 0.511 mmol) and sodium iodide (154 mg, 1.02 mmol) were dissolved in DMF (3 ml) to which was subsequently added sodium hydride (40 mg, 60%, 1.0 mmol) at room temperature. After stirring at room temperature for 10 minutes and then at 60° C. for 3.5 hours, DMF was removed by evaporation. The resulting residue was diluted with water (10 ml) and extracted with ethyl acetate, and the organic layer was washed with water and saturated brine and then dried on anhydrous sodium carbonate. Thereafter, the solvent was removed by evaporation, and the resulting residue was purified by subjecting it to a silica gel column chromatography (methylene chloride:methanol=80:1-ethyl acetate) to obtain 128 mg (54.7%) of the title compound in the form of colorless oil.

Source