반응 #2572

반응 방정식

sodium hydroxide

hydrochloric acid

tin

4-Nitro-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzamide

→

title compound

수율 98.3%

4-Amino-N-{2[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxy-phenyl)benzamide

수율 98.3%

용매

—

ice water

chloroform

methanol

반응 조건

후처리

1. 1
   온도while cooling in an ice bath
2. 2
   기타to remove insoluble materials
3. 3
   세척The resulting residue was washed with chloroform
4. 4
   추출the filtrate was extracted with chloroform
5. 5
   세척the resulting organic layer was washed with water and saturated brine
6. 6
   건조dried on anhydrous sodium sulfate
7. 7
   기타Thereafter, the solvent was removed by evaporation
8. 8
   기타the resulting residue was purified by a silica gel column chromatography (chloroform:methanol=10:1)

실험 절차

4-Nitro-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzamide (264.0 mg, 0.52 mmol) was dissolved in methanol (5 ml) to which were subsequently added concentrated hydrochloric acid (2.0 ml) and tin (powder, 186.0 mg, 1.57 mmol) while cooling in an ice bath. After 1 hour of stirring at room temperature, the reaction solution was poured in ice water, adjusted to pH 9 to 10 with 10% sodium hydroxide aqueous solution, mixed with chloroform and then passed through cerite to remove insoluble materials. The resulting residue was washed with chloroform, the filtrate was extracted with chloroform, and the resulting organic layer was washed with water and saturated brine, and dried on anhydrous sodium sulfate. Thereafter, the solvent was removed by evaporation, and the resulting residue was purified by a silica gel column chromatography (chloroform:methanol=10:1) to obtain 243.0 mg (97.9%) of the title compound in a colorless amorphous form.

출처