N1(O)CCOCC1.[CH3:8][CH:9](NC(C)(C)C)[C:10]([C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([Cl:18])[CH:17]=1)=[O:11].Cl.ClC1C=C(C(=O)CC)C=CC=1.[Br-:36].[Br-].O1CCOCC1>O1CCOCC1.O>[Br:36][CH:9]([CH3:8])[C:10]([C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([Cl:18])[CH:17]=1)=[O:11]
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 2h 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).
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