4'-Hydroxypropiophenone → Ifenprodil

HRID 355079

Reaktionsgleichung

Reaktionsgleichung von HRID 355079
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:4][CH:3]=1.BrBr.[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.C([O-])(=O)C.[Na+].[H][H]>[C].[Pd].C(O)C>[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

Komponenten

8

Edukt 5

HCID 62714'-HydroxypropiophenoneHCID 164584-BenzylpyridineHCID 24408BromineHCID 517045Sodium AcetateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 3689IfenprodilAusbeute 65,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 702EthanolLösungsmittel2×

Versuchsvorschrift

To 10 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 and the reaction liquid was stirred for an additional 10 minutes. To the reaction liquid were then added 7.5 g of 4-benzylpyridine, 100 ml of ethanol and 3.28 g of anhydrous sodium acetate, and the mixture was refluxed under heating for 5 hours. After replacing the air in the reaction container with nitrogen gas, 2.0 g of 10% palladium-carbon were added and hydrogen was then introduced and the mixture was then treated in the same manner as described in Example 20, whereby 8.5 g (55.1%) of ifenprodil were obtained as white crystals.

Aufarbeitung

  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 5 hours
  6. additionwere added
  7. additionthe mixture was then treated in the same manner

Quellen und Nachweise

ORD-Eintrag
ord-ee90227d23154d54b0a4e3d24c92a2b1
Quelldatensatz
uspto-grants-1983_03
Patentnummer
US04377691

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