Reaction #2570

Reaction equation

diethyl azodicarboxylate

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

succinimide

triphenylphosphine

→

title compound

Yield 66.8%

N-{2-[4-(4-Fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)-4-succinimidomethylbenzamide

Yield 66.8%

Solvents

water

THF

Conditions

Workup

1. 1
   Temperaturewhile cooling in an ice bath
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 carbonate
5. 5
   OtherThereafter, the solvent was removed by evaporation
6. 6
   Otherthe resulting residue was purified by a PTLC (chloroform:methanol=20:1)

Procedure

In an atmosphere of argon, N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-4-hydroxymethyl-N-(2-methoxyphenyl)benzamide (54 mg, 0.11 mmol), succinimide (13 mg, 0.132 mmol) and triphenylphosphine (34.6 mg, 0.132 mmol) were dissolved in THF (1 ml) to which was subsequently added dropwise diethyl azodicarboxylate (21 μl, 0.132 mmol) while cooling in an ice bath. After 30 minutes of stirring at room temperature, the reaction solution was diluted with water (10 ml) and extracted with ethyl acetate. The resulting organic layer was washed with water and saturated brine, and dried on anhydrous sodium carbonate. Thereafter, the solvent was removed by evaporation, and the resulting residue was purified by a PTLC (chloroform:methanol=20:1) to obtain 42 mg (66.8%) of the title compound in a light yellow amorphous form.

Source