4'-Hydroxypropiophenone → Ifenprodil

HRID 355078Notes

Reaction equation

HRID 355078 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.C([O-])(=O)C.[Na+].[CH2:19]([C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[H][H]>[C].[Pd].CO.O1CCOCC1>[CH3:10][CH:9]([N:29]1[CH2:30][CH2:31][CH:26]([CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:27][CH2:28]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 72.3%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To 5 ml of dioxane were added 3.0 g of 4'-hydroxypropiophenone. 3.6 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 1.7 g of anhydrous sodium acetate, 3.7 g of 4-benzylpyridine and 40 ml of methanol, and the mixture was refluxed under heating for 5 hours. After replacing the air in the reaction container with nitrogen gas, 60 ml of methanol and 3.0 g of 10% palladium-carbon were added and hydrogen was then introduced and the mixture was stirred for 8 hours at 90°-95° C. under pressure of 20 kg/cm2. The reaction mixture was then treated in the same manner as described in Example 18, whereby 4.7 g (61.0%) 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. additionwere added
  7. stirringthe mixture was stirred for 8 hours at 90°-95° C. under pressure of 20 kg/cm2
  8. additionThe reaction mixture was then treated in the same manner

Sources & evidence

ORD record
ord-25685ddf1c9444339d43b322d2ee3acc
Source dataset
uspto-grants-1983_03
Patent number
US04377691

Reaction notes

Loading…