Triethylamine → 1-[2,4-Bis(trifluoromethyl)phenyl]piperidine-4-carbaldehyde

HRID 1620589Notes

Reaction equation

HRID 1620589 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[N:13]1[CH2:18][CH2:17][CH:16]([CH2:19][OH:20])[CH2:15][CH2:14]1.C(N(CC)CC)C.C(=O)([O-])O.[Na+].C(OCC)(=O)C>CS(C)=O>[F:22][C:2]([F:1])([F:21])[C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:10])[F:11])[CH:6]=[CH:5][C:4]=1[N:13]1[CH2:14][CH2:15][CH:16]([CH:19]=[O:20])[CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 86678761{1-[2,4-Bis(trifluoromethyl)phenyl]piperidin-4-yl}methanol

Product 1

HCID 866787621-[2,4-Bis(trifluoromethyl)phenyl]piperidine-4-carbaldehydeYield 66.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of {1-[2,4-bis(trifluoromethyl)phenyl]piperidin-4-yl}methanol (2.41 g) and triethylamine (3.08 mL) in dimethyl sulfoxide (30 mL) was added sulfur trioxide pyridine complex (3.52 g), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture were added saturated aqueous sodium hydrogen carbonate solution and ethyl acetate, and the organic layer was separated, washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.60 g).

Workup

  1. customthe organic layer was separated
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-fe0a1436ee6d488e971a297b926fb58b
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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