Reacción #2170874

Ecuación de reacción

3,4-dibenzyloxyphenacyl bromide

N-[2-(4-acetamidophenoxy)ethyl]benzylamine

sodium carbonate

ethanol

→

N-benzyl-N-(3,4-dibenzyloxybenzoyl)methyl-2-(4-acetamidophenoxy)ethylamine

Rendimiento 66.9%

Disolventes

isopropanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaunder reflux for 2 hours
2. 2
   Filtraciónfiltered hot
3. 3
   Otroto remove the inorganic sediment
4. 4
   Otroevaporated in vacuo
5. 5
   Otroto afford a thick syrup
6. 6
   Temperaturathe solution cooled
7. 7
   Filtraciónthe precipitated solid then being collected by filtration
8. 8
   workup.ADDITIONTo a hot solution of the solid in fresh isopropanol were added a few milliliters of ethyl acetate
9. 9
   FiltraciónThe crystallized solid was collected by filtration
10. 10
    Lavadowashed in diethyl ether
11. 11
    Otrodried
12. 12
    OtroRecrystallization from an isopropanol/ethyl acetate mixture

Procedimiento

A mixture of 3,4-dibenzyloxyphenacyl bromide (32.8 g.), N-[2-(4-acetamidophenoxy)ethyl]benzylamine (22.8 g.), anhydrous sodium carbonate (8.4 g.) and ethanol (1 liter) was boiled under reflux for 2 hours, then filtered hot to remove the inorganic sediment and evaporated in vacuo to afford a thick syrup. The latter was dissolved in hot isopropanol and the solution cooled, the precipitated solid then being collected by filtration. To a hot solution of the solid in fresh isopropanol were added a few milliliters of ethyl acetate, and the solution was then allowed to cool to room temperature. The crystallized solid was collected by filtration, washed in diethyl ether and dried. Recrystallization from an isopropanol/ethyl acetate mixture afforded N-benzyl-N-(3,4-dibenzyloxybenzoyl)methyl-2-(4-acetamidophenoxy)ethylamine (32.8 g.), m.p. 104°-6° C.

Fuente