Reaktion #2572

Reaktionsgleichung

sodium hydroxide

hydrochloric acid

tin

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

→

title compound

Ausbeute 98.3%

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

Ausbeute 98.3%

Lösungsmittel

—

ice water

chloroform

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwhile cooling in an ice bath
2. 2
   Sonstigeto remove insoluble materials
3. 3
   WaschenThe resulting residue was washed with chloroform
4. 4
   Extraktionthe filtrate was extracted with chloroform
5. 5
   Waschenthe resulting organic layer was washed with water and saturated brine
6. 6
   Trocknendried on anhydrous sodium sulfate
7. 7
   SonstigeThereafter, the solvent was removed by evaporation
8. 8
   Sonstigethe resulting residue was purified by a silica gel column chromatography (chloroform:methanol=10:1)

Vorschrift

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.

Quelle