反応 #2565

反応方程式

1-(2-chloroethyl)-4-(4-fluorobenzoyl)piperidine

N-(2-methoxyphenyl)-p-toluenesulfonamide

sodium iodide

sodium hydride

→

title compound

収率 91.5%

N-{2-[4-(4-Fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)-p-toluenesulfonamide

収率 91.5%

溶媒

DMF

DMF

DMF

反応条件

後処理

1. 1
   その他at room temperature
2. 2
   workup.WAITat 60° C. for 10 minutes
3. 3
   workup.ADDITIONwas added to the reaction solution at 1 hour intervals at 60° C
4. 4
   その他was removed by evaporation
5. 5
   workup.ADDITIONThe thus obtained residue was diluted with water (10 ml)
6. 6
   抽出extracted with ether
7. 7
   洗浄The resulting organic layer was washed with water and saturated brine
8. 8
   乾燥dried on anhydrous sodium carbonate
9. 9
   その他Thereafter, the solvent was removed by evaporation
10. 10
    その他the resulting residue was purified by a silica gel column chromatography (ether:hexane=2:1)

実験手順

In an atmosphere of argon, N-(2-methoxyphenyl)-p-toluenesulfonamide (277 mg, 1.0 mmol) and a catalytically effective amount of sodium iodide were dissolved in DMF (3 ml) to which was subsequently added sodium hydride (44 mg, 60%, 1.1 mmol) at room temperature. After stirring at the same temperature for 30 minutes and then at 60° C. for 10 minutes, 1-(2-chloroethyl)-4-(4-fluorobenzoyl)piperidine (324 mg, 1.2 mmol) which has been divided into 3 portions, each being dissolved in DMF (1 ml), was added to the reaction solution at 1 hour intervals at 60° C. After 1.5 hours of additional stirring at the same temperature, DMF was removed by evaporation. The thus obtained residue was diluted with water (10 ml) and extracted with ether. The resulting organic layer was washed with water and saturated brine, and dried on anhydrous sodium carbonate. Thereafter, the solvent was removed by evaporation, and the resulting residue was purified by a silica gel column chromatography (ether:hexane=2:1) to obtain 467 mg (91.5%) of the title compound in the form of colorless oil.

出典