Trifluoroacetic acid → 1-Benzyl-4-(4-methoxyphenyl)-1,2,3,6-tetrahydropyridine

HRID 1507240Notes

Reaction equation

HRID 1507240 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])=[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.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([N:8]1[CH2:9][CH:10]=[C:11]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[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

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 159073291-Benzyl-4-(4-methoxyphenyl)piperidin-4-ol

Product 1

HCID 106364031-Benzyl-4-(4-methoxyphenyl)-1,2,3,6-tetrahydropyridineYield 89.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-benzyl-4-(4-methoxyphenyl)piperidin-4-ol (7 g, 23.5 mmol) in DCM (150 mL) was added trifluoroacetic acid (2.68 g, 23.5 mmol) and the reaction mixture was stirred at rt overnight. The mixture was then evaporated under reduced pressure and partitioned between 500 mL saturated aqueous sodium bicarbonate and 500 mL of ethyl acetate. The organic layer was separated, dried over Na2SO4, filtered, and evaporated under reduced pressure to yield 1-benzyl-4-(4-methoxyphenyl)-1,2,3,6-tetrahydropyridine (5.9 g, 88% yield). LCMS (method F) RT 2.84 min, 100% AP, m/z 280.4 (M+H+).

Workup

  1. customThe mixture was then evaporated under reduced pressure
  2. custompartitioned between 500 mL saturated aqueous sodium bicarbonate and 500 mL of ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-cb3fc64513f346d6a6f13d7702f9575a
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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