4'-Hydroxypropiophenone → Ifenprodil hydrobromide

HRID 355077

Reaktionsgleichung

Reaktionsgleichung von HRID 355077
O1CCOCC1.[OH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:17])[CH2:15][CH3:16])=[CH:10][CH:9]=1.[Br:18]Br.[CH2:20]([C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CO>[CH3:16][CH:15]([N:30]1[CH2:31][CH2:32][CH:27]([CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:28][CH2:29]1)[CH:14]([OH:17])[C:11]1[CH:12]=[CH:13][C:8]([OH:7])=[CH:9][CH:10]=1.[BrH:18]

Komponenten

6

Edukt 4

HCID 62714'-HydroxypropiophenoneHCID 164584-BenzylpyridineHCID 24408BromineHCID 312751,4-Dioxane

Produkt 1

HCID 12613162Ifenprodil hydrobromideAusbeute 70,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a mixture of 3 ml of dioxane and 1 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 was introduced thereinto at a flow rate of 400 ml/minute for 15 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 11.4 g (70.4%) of ifenprodil hydrobromide were obtained as white crystals.

Aufarbeitung

  1. customThe reaction liquid
  2. stirringwas stirred for an additional 10 minutes
  3. additionnitrogen 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

Quellen und Nachweise

ORD-Eintrag
ord-dfa6965e2cfe46519d388a62cab50ded
Quelldatensatz
uspto-grants-1983_03
Patentnummer
US04377691

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