Potassium Iodide → HCID 23138512, compound

HRID 1171662Notes

Reaction equation

HRID 1171662 reaction equation
[NH:1]1[CH:5]=[C:4](/[CH:6]=[C:7]2\[CH2:8][N:9]([C:14]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:10][CH2:11][CH:12]\2[OH:13])[CH:3]=[N:2]1.Br[CH2:34][C:35]([O:37][CH3:38])=[O:36].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O.O>[CH3:38][O:37][C:35]([CH2:34][N:1]1[CH:5]=[C:4](/[CH:6]=[C:7]2\[CH2:8][N:9]([C:14]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:10][CH2:11][CH:12]\2[OH:13])[CH:3]=[N:2]1)=[O:36]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 23138933HCID 23138933, compound

Product 1

HCID 23138512HCID 23138512, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)-3-[(1H-pyrazol-4-yl)methylidene]-1-(triphenylmethyl)piperidin-4-ol (10.31 g) and methyl bromoacetate (7.0 ml) in N,N-dimethylformamide (150 ml) were added potassium carbonate (10.20 g) and potassium iodide (12.30 g) with stirring at room temperature, and the resulting mixture was refluxed for 1 hour. After water was added, the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate, hexane, and dichloromethane (2:1:1) as the eluent to afford the title compound (4.74 g, yield: 39%) as a pale yellow amorphous solid.

Workup

  1. temperaturethe resulting mixture was refluxed for 1 hour
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous sodium chloride solution
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-7a892c1fb3cd4dec8dc1d2ed88c17809
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

Loading…