반응 #2571

반응 방정식

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

hydrazine hydrate

sodium bicarbonate

→

title compound

수율 76.4%

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

수율 76.4%

용매

ethyl acetate

—

solution

methanol THF

반응 조건

후처리

1. 1
   온도while cooling in an ice bath
2. 2
   기타the organic solvent was removed by evaporation
3. 3
   추출the resulting residue was extracted with methylene chloride
4. 4
   세척The resulting organic layer was washed with saturated sodium bicarbonate aqueous solution and saturated brine
5. 5
   건조dried on anhydrous sodium carbonate
6. 6
   기타followed 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
   기타the solvent was removed by evaporation
10. 10
    기타the resulting reaction solution
11. 11
    추출extracted with ethyl acetate
12. 12
    기타After drying the
13. 13
    추출extract on anhydrous sodium carbonate
14. 14
    기타the solvent was removed by evaporation
15. 15
    기타the resulting light yellow oily residue was purified by a silica gel column chromatography (methylene chloride:methanol=20:1 to 9:1)

실험 절차

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.

출처