Reaktion #2570

Reaktionsgleichung

diethyl azodicarboxylate

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

succinimide

triphenylphosphine

→

title compound

Ausbeute 66.8%

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

Ausbeute 66.8%

Lösungsmittel

water

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwhile cooling in an ice bath
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   WaschenThe resulting organic layer was washed with water and saturated brine
4. 4
   Trocknendried on anhydrous sodium carbonate
5. 5
   SonstigeThereafter, the solvent was removed by evaporation
6. 6
   Sonstigethe resulting residue was purified by a PTLC (chloroform:methanol=20:1)

Vorschrift

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.

Quelle