4'-Hydroxypropiophenone → Ifenprodil

HRID 355087

Reaction equation

HRID 355087 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-])[O-].[K+].[K+].[H][H]>[Pt]=O.CO.O.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

10

Reactant 5

HCID 62714'-HydroxypropiophenoneHCID 11430Potassium CarbonateHCID 164584-BenzylpyridineHCID 24408BromineHCID 178418361HCID 178418361, compound

Product 1

HCID 3689IfenprodilYield 92.3%

Reagents, catalysts & solvents 4

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent2×HCID 962WaterSolventHCID 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, 2.1 g of potassium carbonate, 1 ml of water and 50 ml of methanol, and the mixture was refluxed under heating for 5 hours. After stopping the heating, 25 ml of methanol and 0.2 g of platinum oxide were added and hydrogen was then introduced and the mixture was stirred for 8 hours under pressure of about 1 atm. After completion of the reaction, the reaction mixture was worked up in the same manner as described in Example 46, whereby 12.0 g (77.9%) 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. additionwere added
  7. stirringthe mixture was stirred for 8 hours under pressure of about 1 atm
  8. customAfter completion of the reaction

Sources & evidence

ORD record
ord-e9719236f7bd46719c424a3bcb53e5af
Source dataset
uspto-grants-1983_03
Patent number
US04377691

Linked notes

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