Réaction #2571

Équation de réaction

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

hydrazine hydrate

sodium bicarbonate

→

title compound

Rendement 76.4%

4-Aminomethyl-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzenesulfonamide

Rendement 76.4%

Solvants

ethyl acetate

—

solution

methanol THF

Conditions de réaction

Traitement

1. 1
   Températurewhile cooling in an ice bath
2. 2
   Autrethe organic solvent was removed by evaporation
3. 3
   Extractionthe resulting residue was extracted with methylene chloride
4. 4
   LavageThe resulting organic layer was washed with saturated sodium bicarbonate aqueous solution and saturated brine
5. 5
   Séchagedried on anhydrous sodium carbonate
6. 6
   Autrefollowed by the removal of the solvent by evaporation
7. 7
   workup.ADDITIONTo the resulting residue was added an acetic acid-THF-water (3:1:1) mixture solution (3 ml)
8. 8
   workup.STIRRINGAfter 2 hours of stirring at room temperature
9. 9
   Autrethe solvent was removed by evaporation
10. 10
    Autrethe resulting reaction solution
11. 11
    Extractionextracted with ethyl acetate
12. 12
    AutreAfter drying the
13. 13
    Extractionextract on anhydrous sodium carbonate
14. 14
    Autrethe solvent was removed by evaporation
15. 15
    Autrethe resulting light yellow oily residue was purified by a silica gel column chromatography (methylene chloride:methanol=20:1 to 9:1)

Mode opératoire

N-{2-[4-(4-Fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)-4-phthalimidomethylbenzenesulfonamide (77 mg, 0.117 mmol) was dissolved in a methanol-THF (3:2) mixture solution (2.5 ml) to which was subsequently added hydrazine hydrate (1 ml) while cooling in an ice bath. After 15 minutes of stirring at the same temperature, the organic solvent was removed by evaporation, and the resulting residue was extracted with methylene chloride. The resulting organic layer was washed with saturated sodium bicarbonate aqueous solution and saturated brine, and dried on anhydrous sodium carbonate, followed by the removal of the solvent by evaporation. To the resulting residue was added an acetic acid-THF-water (3:1:1) mixture solution (3 ml). After 2 hours of stirring at room temperature, the solvent was removed by evaporation, and the resulting reaction solution was diluted with ethyl acetate (15 ml), mixed with saturated sodium bicarbonate aqueous solution (5 ml) and then extracted with ethyl acetate. After drying the extract on anhydrous sodium carbonate, the solvent was removed by evaporation, and the resulting light yellow oily residue was purified by a silica gel column chromatography (methylene chloride:methanol=20:1 to 9:1) to obtain 47 mg (76.4%) of the title compound in a colorless oily form.

Source