4'-Hydroxypropiophenone → Ifenprodil hydrobromide

HRID 355082Notes

Reaction equation

HRID 355082 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.C(=O)([O-])O.[K+]>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.[BrH:12]

Participants

8

Reactant 4

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

Product 1

HCID 12613162Ifenprodil hydrobromideYield 66.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 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 6.4 g of 4-benzylpyridine, 1 ml of water, 100 ml of methanol and 4.0 g of potassium hydrogen carbonate, and the mixture was refluxed under heating for 5 hours. The reaction mixture was then treated in the same manner as described in Example 26, whereby 10.6 g (66.4%) 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. additionThe reaction mixture was then treated in the same manner

Sources & evidence

ORD record
ord-b69667c6c86b4a37a70f575b65718208
Source dataset
uspto-grants-1983_03
Patent number
US04377691

Reaction notes

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