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

HRID 11729

Reaktionsgleichung

Reaktionsgleichung von HRID 11729
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:14])=[C:6]([C:8](=[O:13])[CH2:9][CH2:10][C:11]#[N:12])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:24][C:25]([N:27]1[CH2:32][CH:31]([CH3:33])[N:30]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=2)[CH2:29][CH:28]1[CH3:42])=[O:26]>C(#N)C.O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH2:24][C:25]([N:27]2[CH2:32][C@H:31]([CH3:33])[N:30]([CH2:34][C:35]3[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=3)[CH2:29][C@H:28]2[CH3:42])=[O:26])=[C:6]([C:8](=[O:13])[CH2:9][CH2:10][C:11]#[N:12])[CH:7]=1

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 219732762-Chloro-1-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-ethanoneHCID 219733224-(5-Chloro-2-hydroxy-phenyl)-4-oxo-butyronitrile

Produkt 1

HCID 696556954-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-4-oxo-butyronitrileAusbeute 93,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-(5-chloro-2-hydroxy-phenyl)-4-oxo-butyronitrile (0.15 g, 0.70 mmol) in acetonitrile (4 mL) was added potassium carbonate (0.16 g, 1.16 mmol), potassium iodide (0.040 g, 0.24 mmol) and (2-chloro-1-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.21 g, 0.70 mmol). The reaction was stirred for 20 hours at ambient temperature. Tetrahydrofuran (8 mL) was added and solids were removed by filtration. The filtrate was concentrated and the crude product purified by flash chromatography to give the title compound (0.31 g).

Aufarbeitung

  1. customsolids were removed by filtration
  2. concentrationThe filtrate was concentrated
  3. customthe crude product purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f7af4245129340b897705ab8f32f1413
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098212B2

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