1-Benzyl-4-(3,4-dimethoxyphenyl)piperidin-4-ol → 1-Benzyl-4-(3,4-dimethoxyphenyl)-1,2,3,6-tetrahydropyridine

HRID 1272278Notes

Reaction equation

HRID 1272278 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=2)(O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C>[CH2:1]([N:8]1[CH2:9][CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 135355651-Benzyl-4-(3,4-dimethoxyphenyl)piperidin-4-ol

Product 1

HCID 124107571-Benzyl-4-(3,4-dimethoxyphenyl)-1,2,3,6-tetrahydropyridineYield 90%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To acetic acid (130 ml) was added 1-benzyl-4-(3,4-dimethoxyphenyl)piperidine-4-ol (26.0 g, 79.4 mmol) obtained in Reference Example 14. The mixture was refluxed for 3 hours. The reaction mixture was concentrated, and the residue was made to basic with a solution of potassium carbonate and extracted with ethyl acetate. The organic extract was washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residual crystals were washed with hexane to obtain 22.0 g (yield 90%) of the title compound. mp. 94–96° C.

Workup

  1. customobtained in Reference Example 14
  2. temperatureThe mixture was refluxed for 3 hours
  3. concentrationThe reaction mixture was concentrated
  4. extractionextracted with ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with water and saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. washThe residual crystals were washed with hexane

Sources & evidence

ORD record
ord-c0c782e88080432b82482549d7550d20
Source dataset
uspto-grants-2007_04
Patent number
US07208495B2

Reaction notes

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