Bupropion Hydrochloride → alpha-Bromo-3-chloropropiophenone

HRID 24273

反応式

HRID 24273 の反応式
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]

参加物

7

反応物 4

HCID 62884Bupropion HydrochlorideHCID 165345Morpholin-4-olHCID 5871283'-ChloropropiophenoneHCID 222259191,4-Dioxane dibromide

生成物 1

HCID 4992116alpha-Bromo-3-chloropropiophenone収率 85%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒2 回

実験手順

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).

後処理

  1. extractionThe mixture was extracted several times with methylene chloride
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a8c39d2824704ce497deda9dca6a1b3c
出典データセット
uspto-grants-2005_02
特許番号
US06855820B2

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