4'-Hydroxypropiophenone → Ifenprodil hydrobromide

HRID 355074

Reaktionsgleichung

Reaktionsgleichung von HRID 355074
[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>CO>[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]

Komponenten

5

Edukt 3

HCID 62714'-HydroxypropiophenoneHCID 164584-BenzylpyridineHCID 24408Bromine

Produkt 1

HCID 12613162Ifenprodil hydrobromideAusbeute 62,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

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 nitrogen gas was introduced thereinto at a flow rate of 400 ml/minute for 20 minutes at room temperature. 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 8 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.

Aufarbeitung

  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 8 hours
  7. additionThe reaction mixture was then treated in the same manner

Quellen und Nachweise

ORD-Eintrag
ord-d8f0036d11d34ac09cd55d77a248408b
Quelldatensatz
uspto-grants-1983_03
Patentnummer
US04377691

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