Ethanol → Ifenprodil hydrobromide

HRID 355075

Reaction equation

HRID 355075 reaction equation
C(O)C.[OH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:14])[CH2:12][CH3:13])=[CH:7][CH:6]=1.[Br:15]Br.[CH2:17]([C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CO>[CH3:13][CH:12]([N:27]1[CH2:28][CH2:29][CH:24]([CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:25][CH2:26]1)[CH:11]([OH:14])[C:8]1[CH:9]=[CH:10][C:5]([OH:4])=[CH:6][CH:7]=1.[BrH:15]

Participants

6

Reactant 4

HCID 702EthanolHCID 62714'-HydroxypropiophenoneHCID 164584-BenzylpyridineHCID 24408Bromine

Product 1

HCID 12613162Ifenprodil hydrobromideYield 62.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 5 ml of ethanol were added 6.0 g of 4'-hydroxypropiophenone. 6.4 Grams of bromine were added dropwise to the mixture with stirring at room temperature. The reaction liquid was stirred for an additional 10 minutes and then nitrogen gas was introduced thereinto at a flow rate of 100 ml/minute for 30 minutes at 60° C. To the reaction liquid were then added 7.5 g of 4-benzylpyridine and 100 ml of methanol, and the mixture was refluxed under heating for 5 hours. The reaction mixture was then treated in the same manner as described in Example 5, whereby 10.2 g (62.7%) of ifenprodil hydrobromide were obtained as white crystals.

Workup

  1. customThe reaction liquid
  2. stirringwas stirred for an additional 10 minutes
  3. additionnitrogen gas was introduced
  4. customTo the reaction liquid
  5. temperaturethe mixture was refluxed
  6. temperatureunder heating for 5 hours
  7. additionThe reaction mixture was then treated in the same manner

Sources & evidence

ORD record
ord-f693688306ef48c6b846ef47720d99a4
Source dataset
uspto-grants-1983_03
Patent number
US04377691

Linked notes

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