反応 #2571

反応方程式

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

hydrazine hydrate

sodium bicarbonate

→

title compound

収率 76.4%

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

収率 76.4%

溶媒

ethyl acetate

—

solution

methanol THF

反応条件

後処理

1. 1
   温度while cooling in an ice bath
2. 2
   その他the organic solvent was removed by evaporation
3. 3
   抽出the resulting residue was extracted with methylene chloride
4. 4
   洗浄The resulting organic layer was washed with saturated sodium bicarbonate aqueous solution and saturated brine
5. 5
   乾燥dried on anhydrous sodium carbonate
6. 6
   その他followed 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
   その他the solvent was removed by evaporation
10. 10
    その他the resulting reaction solution
11. 11
    抽出extracted with ethyl acetate
12. 12
    その他After drying the
13. 13
    抽出extract on anhydrous sodium carbonate
14. 14
    その他the solvent was removed by evaporation
15. 15
    その他the resulting light yellow oily residue was purified by a silica gel column chromatography (methylene chloride:methanol=20:1 to 9:1)

実験手順

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.

出典