4'-Hydroxypropiophenone → Ifenprodil

HRID 355092Notes

Reaction equation

HRID 355092 reaction equation
C(OCCCC)CCC.[OH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:20])[CH2:18][CH3:19])=[CH:13][CH:12]=1.BrBr.[CH2:23]([C:30]1[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])O.[K+]>CO.O>[CH3:19][CH:18]([N:33]1[CH2:34][CH2:35][CH:30]([CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:31][CH2:32]1)[CH:17]([OH:20])[C:14]1[CH:15]=[CH:16][C:11]([OH:10])=[CH:12][CH:13]=1

Participants

8

Reactant 5

HCID 62714'-HydroxypropiophenoneHCID 8909Butyl etherHCID 164584-BenzylpyridineHCID 24408BromineHCID 516893Potassium Bicarbonate

Product 1

HCID 3689IfenprodilYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To 10 ml of di-n-butyl ether were added 6.0 g of 4'-hydroxypropiophenone. 6.6 Grams of bromine were added dropwise to the mixture with stirring at room temperature, and the reaction liquid was stirred for an additional 10 minutes. To the reaction liquid were then added 7.5 g of 4-benzylpyridine, 4.0 g of potassium hydrogen carbonate, 1 ml of water and 50 ml of methanol, and the mixture was refluxed under heating for 5 hours. After stopping the heating, the reaction mixture was treated in the same manner as described in Example 46, whereby 11.7 g (76.0%) of ifenprodil were obtained as white crystals.

Workup

  1. customthe reaction liquid
  2. stirringwas stirred for an additional 10 minutes
  3. customTo the reaction liquid
  4. temperaturethe mixture was refluxed
  5. temperatureunder heating for 5 hours
  6. additionthe reaction mixture was treated in the same manner

Sources & evidence

ORD record
ord-85ea9f2e4a044fca8b096e1a222cd7ae
Source dataset
uspto-grants-1983_03
Patent number
US04377691

Reaction notes

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