Реакция #2572

Уравнение реакции

sodium hydroxide

hydrochloric acid

tin

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

→

title compound

Выход 98.3%

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

Выход 98.3%

Растворители

—

ice water

chloroform

methanol

Условия реакции

Обработка

1. 1
   Температураwhile cooling in an ice bath
2. 2
   Другоеto remove insoluble materials
3. 3
   ПромывкаThe resulting residue was washed with chloroform
4. 4
   Экстракцияthe filtrate was extracted with chloroform
5. 5
   Промывкаthe resulting organic layer was washed with water and saturated brine
6. 6
   Сушкаdried on anhydrous sodium sulfate
7. 7
   ДругоеThereafter, the solvent was removed by evaporation
8. 8
   Другоеthe resulting residue was purified by a silica gel column chromatography (chloroform:methanol=10:1)

Методика

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.

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