Hydrogen Bromide → 1-Benzyl-4-(6-hydroxynaphth-2-yl)-1,2,3,6-tetrahydropyridine

HRID 380546Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 380546
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](O)([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:24]C)[CH:20]=3)[CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br.[OH-].[Na+]>C(O)(=O)C>[CH2:1]([N:8]1[CH2:9][CH:10]=[C:11]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([OH:24])[CH:20]=3)[CH:15]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 183652491-Benzyl-4-hydroxy-4-(6-methoxynaphth-2-yl)piperidine

Produkt 1

HCID 177857841-Benzyl-4-(6-hydroxynaphth-2-yl)-1,2,3,6-tetrahydropyridineAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of 1.0 gm (2.9 mMol) 1-benzyl-4-hydroxy-4-(6-methoxynaphth-2-yl)piperidine and 0.65 mL (5.8 mMol) 48% hydrobromic acid in 10 mL acetic acid was heated at reflux for 18 hours. The reaction mixture was cooled to room temperature, neutralized with 5N sodium hydroxide, and extracted well with ethyl acetate. The organic extracts were combined, washed with saturated aqueous sodium chloride, dried over sodium sulfate, and concentrated under reduced pressure. The residual solid was suspended in a mixture of ethyl acetate and hexane and the suspension sonicated. The suspension was then filtered to provide 0.57 gm (63%) of the desired compound as a grey solid.

Aufarbeitung

  1. temperatureat reflux for 18 hours
  2. extractionextracted well with ethyl acetate
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionThe residual solid was suspended in a mixture of ethyl acetate and hexane
  7. customthe suspension sonicated
  8. filtrationThe suspension was then filtered

Quellen und Nachweise

ORD-Eintrag
ord-da0803fc86fc4811a83bc0351cb83b18
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06303627B1

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