p-Toluenesulfonic acid → 1-Benzyl-4-(naphth-1-yl)-1,2,3,6-tetrahydropyridine

HRID 380543Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 380543
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](O)([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:9][CH:10]=[C:11]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 183653421-Benzyl-4-hydroxy-4-(naphth-1-yl)piperidine

Produkt 1

HCID 183652301-Benzyl-4-(naphth-1-yl)-1,2,3,6-tetrahydropyridineAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for about 18 hours
  3. custompartitioned between ethyl acetate and 2 N sodium hydroxide
  4. customThe phases were separated
  5. washthe organic phase was washed with saturated aqueous sodium chloride
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-29043cedad614405b1370238136c18be
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06303627B1

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