4'-Hydroxypropiophenone → Ifenprodil hydrobromide

HRID 355091Notes

Reaction equation

HRID 355091 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.[H][H]>[Pt]=O.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

8

Reactant 4

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

Product 1

HCID 12613162Ifenprodil hydrobromideYield 74.1%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolventHCID 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 14.3 g of 4-benzylpyridine and 100 ml of methanol, and the mixture was refluxed under heating for 3 hours. After stopping the heating, 0.5 g of platinum oxide were added and hydrogen was then introduced and the mixture was stirred for 12 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 45, whereby 12.0 g (74.1%) 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 3 hours
  6. additionwere added
  7. stirringthe mixture was stirred for 12 hours under pressure of about 1 atm
  8. customAfter completion of the reaction

Sources & evidence

ORD record
ord-6c8eed605522470398be3532218cc34d
Source dataset
uspto-grants-1983_03
Patent number
US04377691

Reaction notes

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