Reacción #11303

Ecuación de reacción

3′-chloropropiophenone

dioxane dibromide

morpholinol

bupropion hydrochloride

→

2-bromo-3′-chloropropiophenone

Rendimiento 85.0%

Disolventes

dioxane

dioxane

water

Condiciones de reacción

Tratamiento posterior

1. 1
   ExtracciónThe mixture was extracted several times with methylene chloride
2. 2
   SecadoThe combined extracts were dried (Na2SO4)
3. 3
   Concentraciónconcentrated in vacuo

Procedimiento

The racemate of the morpholinol metabolite of bupropion hydrochloride ((+/−)-(2R*,3R*)-2-(3-chlorophenyl)-3,5,5-trimethyl-2-morpholinol hydrochloride) may be synthesized by the following process. To 3′-chloropropiophenone (10.0 g, 0.06 mol) in dioxane (50 mL) was added a solution of dioxane dibromide (14.9 g, 0.06 mol) in dioxane (50 mL). The reaction mixture was stirred for 2 h at ambient temperature and poured into a mixture of ice and water (500 mL). The mixture was extracted several times with methylene chloride. The combined extracts were dried (Na2SO4) and concentrated in vacuo to give 14.8 g (85%) of 2-bromo-3′-chloropropiophenone as a pale yellow oil. This was used without further purification. NMR (300 Mhz, CDCl3); δ 7.99 (m, 1H), 7.90 (d, 1H), 7.57 (d, 1H), 7.44 (t, 1H), 5.22 (q, 1H), 1.91 (t, 3H).

Fuente