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

Reaction equation

HRID 11729 reaction equation
[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

Participants

7

Reactant 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

Product 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-butyronitrileYield 93.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-f7af4245129340b897705ab8f32f1413
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Linked notes

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