4'-Hydroxypropiophenone → Ifenprodil hydrobromide

HRID 355080Notes

Reaction equation

HRID 355080 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+].[K+]>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

7

Reactant 4

HCID 62714'-HydroxypropiophenoneHCID 11430Potassium CarbonateHCID 164584-BenzylpyridineHCID 24408Bromine

Product 1

HCID 12613162Ifenprodil hydrobromideYield 75%

Reagents, catalysts & solvents 2

HCID 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 5 minutes. To the reaction liquid were then added 7.5 g of 4-benzylpyridine, 100 ml of methanol and 2.0 g of potassium 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 12.2 g (75.0%) of ifenprodil hydrobromide were obtained as white crystals.

Workup

  1. customthe reaction liquid
  2. stirringwas stirred for an additional 5 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-6590c382d6dd40e6b40538475af055ab
Source dataset
uspto-grants-1983_03
Patent number
US04377691

Reaction notes

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