4'-Hydroxypropiophenone → Ifenprodil

HRID 355086

Reaktionsgleichung

Reaktionsgleichung von HRID 355086
C(OCCCC)CCC.[OH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:20])[CH2:18][CH3:19])=[CH:13][CH:12]=1.BrBr.[CH2:23]([C:30]1[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CO>[CH3:19][CH:18]([N:33]1[CH2:34][CH2:35][CH:30]([CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:31][CH2:32]1)[CH:17]([OH:20])[C:14]1[CH:15]=[CH:16][C:11]([OH:10])=[CH:12][CH:13]=1

Komponenten

6

Edukt 4

HCID 62714'-HydroxypropiophenoneHCID 8909Butyl etherHCID 164584-BenzylpyridineHCID 24408Bromine

Produkt 1

HCID 3689IfenprodilAusbeute 86,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To 15 ml of di-n-butyl ether were added 6.0 g of 4'-hydroxypropiophenone. 6.6 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 was introduced thereinto at a flow rate of 200 ml/minute for one hour at room temperature. To the treaction 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. After stopping the heating, the reaction mixture was treated in the same manner as described in Example 35, whereby 11.3 g (73.4%) of ifenprodil were obtained as white crystals.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-32383a483a3546a4a3726561f3d84def
Quelldatensatz
uspto-grants-1983_03
Patentnummer
US04377691

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