Reaktion #2571

Reaktionsgleichung

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

hydrazine hydrate

sodium bicarbonate

→

title compound

Ausbeute 76.4%

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

Ausbeute 76.4%

Lösungsmittel

ethyl acetate

—

solution

methanol THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwhile cooling in an ice bath
2. 2
   Sonstigethe organic solvent was removed by evaporation
3. 3
   Extraktionthe resulting residue was extracted with methylene chloride
4. 4
   WaschenThe resulting organic layer was washed with saturated sodium bicarbonate aqueous solution and saturated brine
5. 5
   Trocknendried on anhydrous sodium carbonate
6. 6
   Sonstigefollowed 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
   Sonstigethe solvent was removed by evaporation
10. 10
    Sonstigethe resulting reaction solution
11. 11
    Extraktionextracted with ethyl acetate
12. 12
    SonstigeAfter drying the
13. 13
    Extraktionextract on anhydrous sodium carbonate
14. 14
    Sonstigethe solvent was removed by evaporation
15. 15
    Sonstigethe resulting light yellow oily residue was purified by a silica gel column chromatography (methylene chloride:methanol=20:1 to 9:1)

Vorschrift

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.

Quelle