Methyl iodide → 4-(N-Methylacetylamino)-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(4-methoxyphenyl)benzamide

HRID 2513Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2513
[C:1]([NH:4][C:5]1[CH:38]=[CH:37][C:8]([C:9]([N:11]([CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][CH:25]([C:28](=[O:36])[C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[CH2:24][CH2:23]2)[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[H-].[Na+].[CH3:41]I.[Cl-].[NH4+]>C1COCC1>[CH3:41][CH2:2][C:1]([NH:4][C:5]1[CH:38]=[CH:37][C:8]([C:9]([N:11]([CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][CH:25]([C:28](=[O:36])[C:29]3[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=3)[CH2:24][CH2:23]2)[C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)=[O:10])=[CH:7][CH:6]=1)=[O:3]

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 196898214-Acetylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(4-methoxyphenyl)benzamide

Produkt 1

HCID 196898954-(N-Methylacetylamino)-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(4-methoxyphenyl)benzamideAusbeute 80,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-Acetylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(4-methoxyphenyl)benzamide (155.0 mg, 0.30 mmol) was dissolved in THF (3.0 ml) to which were subsequently added 60% sodium hydride {28.0 mg, 0.70 mmol) and methyl iodide (0.060 ml, 1.00 mmol) at room temperature, followed by 2 hours of stirring. The reaction solution was mixed with saturated ammonium chloride aqueous solution and extracted with ethyl acetate. 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 recrystallized from methanol-ether to obtain 128.0 mg (80.4%) of the title compound in a colorless powder form.

Aufarbeitung

  1. customat room temperature
  2. extractionextracted with ethyl acetate
  3. washThe resulting organic layer was washed with water and saturated brine
  4. dry with materialdried on anhydrous sodium sulfate
  5. customThereafter, the solvent was removed by evaporation
  6. customthe resulting residue was recrystallized from methanol-ether

Quellen und Nachweise

ORD-Eintrag
ord-325ebeb3b83e42ed8fa3b3afdd734121
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728835

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