4'-Hydroxypropiophenone → Ifenprodil

HRID 355090Notes

Reaction equation

HRID 355090 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:4][CH:3]=1.BrBr.[CH2:14]([C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])(=O)C.[Na+].[H][H]>[Pt]=O.C(O)C.O1CCOCC1>[CH3:10][CH:9]([N:24]1[CH2:25][CH2:26][CH:21]([CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:22][CH2:23]1)[CH:8]([OH:11])[C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1

Participants

9

Reactant 5

HCID 62714'-HydroxypropiophenoneHCID 164584-BenzylpyridineHCID 24408BromineHCID 517045Sodium AcetateHCID 178418361HCID 178418361, compound

Product 1

HCID 3689IfenprodilYield 83.8%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To 4 ml of dioxane were added 6.0 g of 4'-hydroxypropiophenone. 6.8 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, 3.3 g of anhydrous sodium acetate and 100 ml of ethanol, and the mixture was refluxed under heating for 3 hours. After stopping the heating, 0.5 g of platinum oxide and 200 ml of ethanol were added and hydrogen was then introduced and the mixture was stirred for 9 hours under pressure of about 1 atm. After completion of the reaction, the reaction mixture was treated in the same manner as described in Example 46, whereby 10.9 g (70.8%) 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 3 hours
  6. additionwere added
  7. stirringthe mixture was stirred for 9 hours under pressure of about 1 atm
  8. customAfter completion of the reaction
  9. additionthe reaction mixture was treated in the same manner

Sources & evidence

ORD record
ord-3876a71b6d704d1d8bf9d6ec30e148d3
Source dataset
uspto-grants-1983_03
Patent number
US04377691

Reaction notes

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