반응 #2570

반응 방정식

diethyl azodicarboxylate

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

succinimide

triphenylphosphine

→

title compound

수율 66.8%

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

수율 66.8%

용매

water

THF

반응 조건

후처리

1. 1
   온도while cooling in an ice bath
2. 2
   추출extracted with ethyl acetate
3. 3
   세척The resulting organic layer was washed with water and saturated brine
4. 4
   건조dried on anhydrous sodium carbonate
5. 5
   기타Thereafter, the solvent was removed by evaporation
6. 6
   기타the resulting residue was purified by a PTLC (chloroform:methanol=20:1)

실험 절차

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.

출처