Reacción #2550

ord-e6f09e6358c645c8a45e3f4af446ce3d

Ecuación de reacción

COc1ccccc1NC(=O)c1ccc(CCl)cc1
4-chloromethyl-N-(2-methoxyphenyl)benzamide
CNC
dimethylamine
COc1ccccc1NC(=O)c1ccc(CN(C)C)cc1
title compound
Rendimiento 100.0%
COc1ccccc1NC(=O)c1ccc(CN(C)C)cc1
N-(2-Methoxyphenyl)-4-dimethylaminomethylbenzamide
Rendimiento 100.0%

Disolventes

Condiciones de reacción

Temperatura
80°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroequipped with a cold finger
  2. 2
    Otrosubsequent removal of dioxane
  3. 3
    Otroby evaporation
  4. 4
    workup.ADDITIONthe resulting residue was diluted with ethyl acetate (30 ml)
  5. 5
    SecadoThe thus diluted solution was dried on anhydrous sodium carbonate
  6. 6
    Otrothe resulting residue was purified

Procedimiento

In an atmosphere of argon, 4-chloromethyl-N-(2-methoxyphenyl)benzamide (276 mg, 1.0 mmol) was put into a 25 ml capacity eggplant type flask equipped with a cold finger and dissolved in dioxane (3 ml), followed by the addition of 50% dimethylamine aqueous solution (3 ml) at room temperature. After 2.5 hours of stirring at 80° C. and subsequent removal of dioxane by evaporation, the resulting residue was diluted with ethyl acetate (30 ml). The thus diluted solution was dried on anhydrous sodium carbonate, and the resulting residue was purified by subjecting it to a silica gel column chromatography (ether-ethyl acetate-ethyl acetate:methanol=10:1) to obtain 284 mg (100%) of the title compound in the form of colorless oil.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05728835uspto-grants-1998_03