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

HRID 2469
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2469
[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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

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

Produkt 1

HCID 19689911N-{2-[4-(4-Fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)-p-toluenesulfonamideAusbeute 91,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-7e6ae5c11c3c403ba17edba9a968e45c
Quelldatensatz
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05728835

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