Isopropyl iodide → HCID 46866329, compound

HRID 1913888Notes

Reaction equation

HRID 1913888 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)=[CH:16][CH:17]=3)[CH2:12][CH2:11][C:10]2=[O:26])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].I[CH:34]([CH3:36])[CH3:35]>CN(C)C=O.O>[F:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH:20]4[CH2:21][CH2:22][N:23]([CH:34]([CH3:36])[CH3:35])[CH2:24][CH2:25]4)=[CH:16][CH:17]=3)[CH2:12][CH2:11][C:10]2=[O:26])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 66684102HCID 66684102, compound

Product 1

HCID 46866329HCID 46866329, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 1-(4-fluorophenyl)-6-(piperidin-4-yloxy)-3,4-dihydroquinolin-2(1H)-one hydrochloride prepared in Example 7-(3) (0.30 g), potassium carbonate (0.55 g) and 2-iodopropane (0.68 g) in N,N-dimethylformamide (10 mL) was stirred at 100° C. for 1 hour. The reaction mixture was cooled to room temperature, diluted with water and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluting solvent: chloroform→chloroform/methanol=4/1) to give the titled compound (0.16 g, 52%) as a colorless solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (eluting solvent: chloroform→chloroform/methanol=4/1)

Sources & evidence

ORD record
ord-d0cc567b239a4be4b586c2536245707c
Source dataset
uspto-grants-2013_12
Patent number
US08609847B2

Reaction notes

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