Реакция #2570

Уравнение реакции

diethyl azodicarboxylate

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

succinimide

triphenylphosphine

→

title compound

Выход 66.8%

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

Выход 66.8%

Растворители

water

THF

Условия реакции

Обработка

1. 1
   Температураwhile cooling in an ice bath
2. 2
   Экстракцияextracted with ethyl acetate
3. 3
   ПромывкаThe resulting organic layer was washed with water and saturated brine
4. 4
   Сушкаdried on anhydrous sodium carbonate
5. 5
   ДругоеThereafter, the solvent was removed by evaporation
6. 6
   Другоеthe resulting residue was purified by a PTLC (chloroform:methanol=20:1)

Методика

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.

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