Potassium Iodide → 2-(4-Chloro-2-nitro-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone

HRID 480186

反応式

HRID 480186 の反応式
COC(=O)[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[O:11][CH2:12][C:13]([N:15]1[CH2:20][C@H:19]([CH3:21])[N:18]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH2:17][C@H:16]1[CH3:30])=[O:14].[N+:32](C1C=C(Cl)C=CC=1O)([O-:34])=[O:33].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(=O)CC.O>[Cl:10][C:8]1[CH:7]=[CH:6][C:5]([O:11][CH2:12][C:13]([N:15]2[CH2:20][C@H:19]([CH3:21])[N:18]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[CH2:17][C@H:16]2[CH3:30])=[O:14])=[C:4]([N+:32]([O-:34])=[O:33])[CH:9]=1

参加物

7

反応物 4

HCID 4875Potassium IodideHCID 69804-Chloro-2-nitrophenolHCID 11430Potassium CarbonateHCID 11487716rel-Methyl 5-chloro-2-[2-[(2R,5S)-4-[(4-fluorophenyl)methyl]-2,5-dimethyl-1-piperazinyl]-2-oxoethoxy]benzoate

生成物 1

HCID 444315252-(4-Chloro-2-nitro-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone収率 93%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6569Methyl Ethyl Ketone溶媒

実験手順

To a solution of (2R, 5S)-5-chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzoic acid methyl ester (1.0 g, 3.35 mmol) in butanone (35 ml) was added 2-nitro-4-chlorophenol (0.639 g, 3.69 mmol), potassium carbonate (0.925 g, 6.7 mmol) and potassium iodide (0.556 g, 3.35 mmol). The reaction mixture was heated at reflux overnight. The reaction mixture was then cooled, diluted with water and extracted with ethyl acetate. The combined organics were dried over magnesium sulfate, filtered and concentrated to give an orange oil. Chromatography on silica gel gave the title compound (1.35 g, 93% yield).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. temperatureThe reaction mixture was then cooled
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organics were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give an orange oil

出典と根拠

ORDレコード
ord-1089e2043a264e1895e01c690b11c3aa
出典データセット
uspto-grants-2003_11
特許番号
US06649611B2

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