Methanol → Ifenprodil hydrobromide

HRID 355076

Reaction equation

HRID 355076 reaction equation
CO.[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:13])[CH2:11][CH3:12])=[CH:6][CH:5]=1.[Br:14]Br.[CH2:16]([C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)C>[CH3:12][CH:11]([N:26]1[CH2:27][CH2:28][CH:23]([CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:24][CH2:25]1)[CH:10]([OH:13])[C:7]1[CH:8]=[CH:9][C:4]([OH:3])=[CH:5][CH:6]=1.[BrH:14]

Participants

6

Reactant 4

HCID 887MethanolHCID 62714'-HydroxypropiophenoneHCID 164584-BenzylpyridineHCID 24408Bromine

Product 1

HCID 12613162Ifenprodil hydrobromideYield 65.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 5 ml of methanol 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 air was introduced thereinto at a flow rate of 200 ml/minute for 30 minutes at room temperature. To the reaction liquid were then added 7.5 g of 4-benzylpyridine and 100 ml of ethanol, and the mixture was refluxed under heating for 5 hours. The reaction mixture was treated in the same manner as described in Example 5, whereby 10.7 g (65.8%) of ifenprodil hydrobromide were obtained as white crystals.

Workup

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

Sources & evidence

ORD record
ord-f3f83a38be1b4b6891216f27cbc38c49
Source dataset
uspto-grants-1983_03
Patent number
US04377691

Linked notes

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