تفاعل #2571

معادلة التفاعل

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

hydrazine hydrate

sodium bicarbonate

→

title compound

المردود 76.4%

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

المردود 76.4%

المذيبات

ethyl acetate

—

solution

methanol THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwhile cooling in an ice bath
2. 2
   أخرىthe organic solvent was removed by evaporation
3. 3
   استخلاصthe resulting residue was extracted with methylene chloride
4. 4
   غسيلThe resulting organic layer was washed with saturated sodium bicarbonate aqueous solution and saturated brine
5. 5
   تجفيفdried on anhydrous sodium carbonate
6. 6
   أخرىfollowed 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
   أخرىthe solvent was removed by evaporation
10. 10
    أخرىthe resulting reaction solution
11. 11
    استخلاصextracted with ethyl acetate
12. 12
    أخرىAfter drying the
13. 13
    استخلاصextract on anhydrous sodium carbonate
14. 14
    أخرىthe solvent was removed by evaporation
15. 15
    أخرىthe resulting light yellow oily residue was purified by a silica gel column chromatography (methylene chloride:methanol=20:1 to 9:1)

الإجراء التجريبي

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.

المصدر