Reaction #2572

Reaction equation

sodium hydroxide

hydrochloric acid

tin

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

→

title compound

Yield 98.3%

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

Yield 98.3%

Solvents

—

ice water

chloroform

methanol

Conditions

Workup

1. 1
   Temperaturewhile cooling in an ice bath
2. 2
   Otherto remove insoluble materials
3. 3
   WashThe resulting residue was washed with chloroform
4. 4
   Extractionthe filtrate was extracted with chloroform
5. 5
   Washthe resulting organic layer was washed with water and saturated brine
6. 6
   Dryingdried on anhydrous sodium sulfate
7. 7
   OtherThereafter, the solvent was removed by evaporation
8. 8
   Otherthe resulting residue was purified by a silica gel column chromatography (chloroform:methanol=10:1)

Procedure

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.

Source