Potassium Iodide → (2R,5S)-5-Chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzaldehyde

HRID 480193

反応式

HRID 480193 の反応式
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH:9]([CH3:11])[N:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH2:7][CH:6]1[CH3:20])=[O:4].[Cl:21][C:22]1[CH:29]=[C:26]([CH:27]=[O:28])[C:25]([OH:30])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C.[Cl-].[Na+].O>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([O:30][CH2:2][C:3]([N:5]2[CH2:10][C@H:9]([CH3:11])[N:8]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[CH2:7][C@H:6]2[CH3:20])=[O:4])=[C:26]([CH:29]=1)[CH:27]=[O:28]

参加物

7

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehydeHCID 219732762-Chloro-1-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-ethanone

生成物 1

HCID 53673807(2R,5S)-5-Chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzaldehyde収率 85%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
100 °C

実験手順

To a solution of 2-chloro-1-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-ethanone (2.87 g, 9.6 mmol) in DMF (20 mL) was added 5-chlorosalicylaldehyde (1.65 g, 10.5 mmol), potassium carbonate (2.64 g, 19.2 mmol) and potassium iodide (1.59 g, 9.6 mmol). The resulting mixture was heated to 100° C. for 12 hours. The reaction was cooled, diluted with saturated aqueous brine and extracted with ethyl acetate (3×). The combined organics were dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo to give crude product. Purification via chromatography on silica gel (15% EtOAc/Hexanes) gave the title compound 3.40 g, 85% yield.)

後処理

  1. temperatureThe reaction was cooled
  2. extractionextracted with ethyl acetate (3×)
  3. dry with materialThe combined organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto give crude product
  7. customPurification via chromatography on silica gel (15% EtOAc/Hexanes)

出典と根拠

ORDレコード
ord-75890e2ef89f4f75a97921c7e64b3dc4
出典データセット
uspto-grants-2003_11
特許番号
US06649611B2

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