Реакция #2571

Уравнение реакции

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

hydrazine hydrate

sodium bicarbonate

→

title compound

Выход 76.4%

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

Выход 76.4%

Растворители

ethyl acetate

—

solution

methanol THF

Условия реакции

Обработка

1. 1
   Температураwhile cooling in an ice bath
2. 2
   Другоеthe organic solvent was removed by evaporation
3. 3
   Экстракцияthe resulting residue was extracted with methylene chloride
4. 4
   ПромывкаThe resulting organic layer was washed with saturated sodium bicarbonate aqueous solution and saturated brine
5. 5
   Сушкаdried on anhydrous sodium carbonate
6. 6
   Другоеfollowed 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
   Другоеthe solvent was removed by evaporation
10. 10
    Другоеthe resulting reaction solution
11. 11
    Экстракцияextracted with ethyl acetate
12. 12
    ДругоеAfter drying the
13. 13
    Экстракцияextract on anhydrous sodium carbonate
14. 14
    Другоеthe solvent was removed by evaporation
15. 15
    Другоеthe resulting light yellow oily residue was purified by a silica gel column chromatography (methylene chloride:methanol=20:1 to 9:1)

Методика

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.

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