Acetic Acid → 1-Benzyl-4-[4-(trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine

HRID 856049Notes

Reaction equation

HRID 856049 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)(O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(O)(=O)C>C(Cl)Cl>[CH2:1]([N:8]1[CH2:9][CH:10]=[C:11]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([F:24])([F:22])[F:23])=[CH:19][CH:20]=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 176Acetic AcidHCID 313Hydrochloric AcidHCID 21559974HCID 21559974, compound

Product 1

HCID 161275071-Benzyl-4-[4-(trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridineYield 80.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-benzyl-4-(4-trifluoromethylphenyl)piperidin-4-ol (692 mg, 2.06 mmol) prepared in Reference Example 95, concentrated hydrochloric acid (4.5 ml) and acetic acid (10 ml) was heated under reflux overnight. The reaction mixture was allowed to return to room temperature, and diluted with methylene chloride. The mixture was washed with water, 10% sodium hydroxide aqueous solution and brine, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/acetone=4/1) to afford 1-benzyl-4-(4-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine (528 mg, yield 80%) as a pale yellow crystalline powder.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. customto return to room temperature
  4. washThe mixture was washed with water, 10% sodium hydroxide aqueous solution and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (n-hexane/acetone=4/1)

Sources & evidence

ORD record
ord-47a25e8fceaf44d888abd38de6464c33
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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