Reaktion #467725

Reaktionsgleichung

1-benzyl-4-hydroxy-4-(naphth-1-yl)piperidine

p-toluenesulfonic acid

→

desired compound

Ausbeute 94.0%

1-benzyl-4-(naphth-1-yl)-1,2,3,6-tetrahydropyridine

Ausbeute 94.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturat reflux for about 18 hours
3. 3
   Sonstigepartitioned between ethyl acetate and 2 N sodium hydroxide
4. 4
   SonstigeThe phases were separated
5. 5
   Waschenthe organic phase was washed with saturated aqueous sodium chloride
6. 6
   Trocknendried over sodium sulfate
7. 7
   Einengenconcentrated under reduced pressure

Vorschrift

A mixture of 2.8 gm (8.8 mMol) 1-benzyl-4-hydroxy-4-(naphth-1-yl)piperidine and 3.36 gm (17.6 mMol) p-toluenesulfonic acid in 50 mL toluene was heated at reflux for about 18 hours. The reaction mixture was then cooled to room temperature and partitioned between ethyl acetate and 2 N sodium hydroxide. The phases were separated and the organic phase was washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under reduced pressure to provide 2.47 gm (94%) of the desired compound as an orange oil.

Quelle