4'-Hydroxypropiophenone → Ifenprodil hydrobromide

HRID 355081Notes

Reaction equation

HRID 355081 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.[Br:12]Br.[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.[OH-].[K+].[H][H]>[C].[Pd].CO.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.[BrH:12]

Participants

9

Reactant 5

HCID 62714'-HydroxypropiophenoneHCID 14797Potassium HydroxideHCID 164584-BenzylpyridineHCID 24408BromineHCID 178418361HCID 178418361, compound

Product 1

HCID 12613162Ifenprodil hydrobromideYield 74.4%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To 4 ml of dioxane were added 6.0 g of 4'-hydroxypropiophenone. 6.4 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, 100 ml of methanol, and 2.8 ml of 10 N potassium hydroxide solution, and the mixture was refluxed under heating for 5 hours. After replacing the air in the reaction container with nitrogen gas, 3.0 g of 10% palladium-carbon were added and hydrogen was then introduced and the mixture was stirred for 8 hours at 60°-70° C. under pressure of 50 kg/cm2. The reaction mixture was then treated in the same manner as described in Example 26, whereby 12.1 g (74.4%) of ifenprodil hydrobromide 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 60°-70° C. under pressure of 50 kg/cm2
  8. additionThe reaction mixture was then treated in the same manner

Sources & evidence

ORD record
ord-e972ede761d94d70939fc00f5a2ca7cc
Source dataset
uspto-grants-1983_03
Patent number
US04377691

Reaction notes

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