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

HRID 2469

반응식

HRID 2469 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11].[I-].[Na+].[H-].[Na+].Cl[CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][CH:30]([C:33](=[O:41])[C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)[CH2:29][CH2:28]1>CN(C=O)C>[F:40][C:37]1[CH:36]=[CH:35][C:34]([C:33]([CH:30]2[CH2:31][CH2:32][N:27]([CH2:26][CH2:25][N:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[S:10]([C:13]3[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=3)(=[O:12])=[O:11])[CH2:28][CH2:29]2)=[O:41])=[CH:39][CH:38]=1

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 241731N-(2-Methoxyphenyl)-4-methylbenzenesulfonamideHCID 10516150Methanone, [1-(2-chloroethyl)-4-piperidinyl](4-fluorophenyl)-

생성물 1

HCID 19689911N-{2-[4-(4-Fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)-p-toluenesulfonamide수율 91.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

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.

후처리

  1. customat room temperature
  2. waitat 60° C. for 10 minutes
  3. additionwas added to the reaction solution at 1 hour intervals at 60° C
  4. customwas removed by evaporation
  5. additionThe thus obtained residue was diluted with water (10 ml)
  6. extractionextracted with ether
  7. washThe resulting organic layer was washed with water and saturated brine
  8. dry with materialdried on anhydrous sodium carbonate
  9. customThereafter, the solvent was removed by evaporation
  10. customthe resulting residue was purified by a silica gel column chromatography (ether:hexane=2:1)

출처 및 근거

ORD 기록
ord-7e6ae5c11c3c403ba17edba9a968e45c
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728835

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