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

HRID 380546Notes

Reaction equation

HRID 380546 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-da0803fc86fc4811a83bc0351cb83b18
Source dataset
uspto-grants-2001_10
Patent number
US06303627B1

Reaction notes

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