Reacción #362102

Ecuación de reacción

4-(3-chlorobenzyloxy)phenetylamine hydrochloride

chloroacetamide

potassium carbonate

HCl

→

[4-(3-chlorobenzyloxy)phenetyl]aminoacetamide, hydrochloride

Disolventes

ethanol

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter heating
2. 2
   Temperaturato reflux
3. 3
   FiltraciónThe hot mixture is filtered
4. 4
   Otroevaporated to dryness
5. 5
   Otrothe crude residue chromatographed on silica gel (eluant CHCl3/MeOH/conc. NH4OH; 97/3/0.3)
6. 6
   OtroThe free compound obtained (20.2 g; 60.7%)

Procedimiento

31 g (0.104 mol) of 4-(3-chlorobenzyloxy)phenetylamine hydrochloride are suspended in 450 ml of anhydrous ethanol. To this mixture, 9.7 g (0.104 mol) of chloroacetamide and 28.8 g (0.208 mol) of anhydrous potassium carbonate are added. After heating to reflux, stirring is continued for 40 hours. The hot mixture is filtered, then evaporated to dryness and the crude residue chromatographed on silica gel (eluant CHCl3/MeOH/conc. NH4OH; 97/3/0.3). The free compound obtained (20.2 g; 60.7%) is treated with gaseous HCl in ethanol to give a quantitative yield of the corresponding [4-(3-chlorobenzyloxy)phenetyl]aminoacetamide, hydrochloride, m.p. 248°-251° C. Analogously the following compound can be obtained, starting from the corresponding primary amine:

Fuente