Réaction #2609

ord-325ebeb3b83e42ed8fa3b3afdd734121

Équation de réaction

[Cl-].[NH4+]
ammonium chloride
[H-].[Na+]
sodium hydride
COc1ccc(N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)C(=O)c2ccc(NC(C)=O)cc2)cc1
4-Acetylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(4-methoxyphenyl)benzamide
CI
methyl iodide
CCC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccc(OC)cc2)cc1
title compound
Rendement 80.4%
CCC(=O)Nc1ccc(C(=O)N(CCN2CCC(C(=O)c3ccc(F)cc3)CC2)c2ccc(OC)cc2)cc1
4-(N-Methylacetylamino)-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(4-methoxyphenyl)benzamide
Rendement 80.4%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autreat room temperature
  2. 2
    Extractionextracted with ethyl acetate
  3. 3
    LavageThe resulting organic layer was washed with water and saturated brine
  4. 4
    Séchagedried on anhydrous sodium sulfate
  5. 5
    AutreThereafter, the solvent was removed by evaporation
  6. 6
    Autrethe resulting residue was recrystallized from methanol-ether

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05728835uspto-grants-1998_03