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

HRID 480186

반응식

HRID 480186 반응식
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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6569Methyl Ethyl Ketone용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1089e2043a264e1895e01c690b11c3aa
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06649611B2

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