Potassium Carbonate → HCID 20084223, compound

HRID 484340Notes

Reaction equation

HRID 484340 reaction equation
[CH:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:24][C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:26]=1>CN(C)C=O>[CH:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:24][C:25]3[CH:34]=[CH:33][C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]=3)=[CH:11][CH:10]=2)=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 12299666HCID 12299666, compound

Product 1

HCID 20084223HCID 20084223, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

7.85 g (38.4 mmol) of 4-hydroxyphenyl cyclohexyl ketone are heated under reflux for 2 h after addition of 12 g (86.8 mmol) of potassium carbonate and 200 ml of dimethylformamide. 8.54 g (39.9 mmol) of 2-chloromethylquinoline hydrochloride are then added at room temperature. The reaction mixture is stirred at 100° C. for 7 h and subsequently concentrated in vacuo. The residue is taken up in dichloromethane, and the organic phase is washed with water, dried over sodium sulphate and concentrated in vacuo. A column chromatographic purification on silica gel using dichloromethane/methanol (50:1) follows.

Workup

  1. temperatureunder reflux for 2 h
  2. concentrationsubsequently concentrated in vacuo
  3. washthe organic phase is washed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customA column chromatographic purification on silica gel

Sources & evidence

ORD record
ord-224547cc74fc4d35a724470deb32d6f3
Source dataset
uspto-grants-1993_07
Patent number
US05231103

Reaction notes

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