反応 #2572

反応方程式

sodium hydroxide

hydrochloric acid

tin

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

→

title compound

収率 98.3%

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

収率 98.3%

溶媒

—

ice water

chloroform

methanol

反応条件

後処理

1. 1
   温度while cooling in an ice bath
2. 2
   その他to remove insoluble materials
3. 3
   洗浄The resulting residue was washed with chloroform
4. 4
   抽出the filtrate was extracted with chloroform
5. 5
   洗浄the resulting organic layer was washed with water and saturated brine
6. 6
   乾燥dried on anhydrous sodium sulfate
7. 7
   その他Thereafter, the solvent was removed by evaporation
8. 8
   その他the resulting residue was purified by a silica gel column chromatography (chloroform:methanol=10:1)

実験手順

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.

出典