4'-Hydroxypropiophenone → Ifenprodil hydrobromide

HRID 355085Notes

Reaction equation

HRID 355085 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.C(O)C.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 66%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent2×HCID 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. The reaction liquid was stirred for an additional 5 minutes and then air was introduced thereinto at a flow rate of 100 ml/minute for one hour at 60° C. To the reaction liquid were then added 8.1 g of 4-benzylpyridine and 100 ml of ethanol, and the mixture was refluxed under heating for 5 hours. After stopping the heating, 0.3 g of platinum oxide and 200 ml of ethanol 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 treated in the same manner as described in Example 34, whereby 10.7 g (66.0%) of ifenprodil hydrobromide were obtained as white crystals.

Workup

  1. customThe reaction liquid
  2. stirringwas stirred for an additional 5 minutes
  3. additionair was introduced
  4. customTo the reaction liquid
  5. temperaturethe mixture was refluxed
  6. temperatureunder heating for 5 hours
  7. additionwere added
  8. stirringthe mixture was stirred for 12 hours under pressure of about 1 atm
  9. customAfter completion of the reaction
  10. additionthe reaction mixture was treated in the same manner

Sources & evidence

ORD record
ord-361a21eb711043509c62b0e8183a3605
Source dataset
uspto-grants-1983_03
Patent number
US04377691

Reaction notes

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