1-Benzylpiperidine-4-carbaldehyde → 1-(1-Benzylpiperidin-4-yl)-2-[2-(trifluoromethyl)phenyl]ethanone

HRID 914851Notes

Reaction equation

HRID 914851 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O.C[O-].[K+].[CH2:16]([N:23]1[CH2:28][CH2:27][CH:26]([CH:29]=[O:30])[CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CO>[CH2:16]([N:23]1[CH2:28][CH2:27][CH:26]([C:29](=[O:30])[CH2:5][C:4]2[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=2[C:2]([F:12])([F:11])[F:1])[CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 895841-Benzylpiperidine-4-carbaldehydeHCID 123067o-(Trifluoromethyl)benzaldehydeHCID 23664618Potassium methoxide

Product 1

HCID 222479231-(1-Benzylpiperidin-4-yl)-2-[2-(trifluoromethyl)phenyl]ethanoneYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

After dissolving 2.57 g of 2-(trifluoromethyl)benzaldehyde in 15 ml of methanol, 2.75 g of p-toluenesulfonyl hydrazide was added, the mixture was stirred at room temperature for 2 hours, and then 1.09 g of potassium methoxide and a methanol solution (4 ml) of 1.50 g of 1-benzylpiperidine-4-carboxaldehyde was added, and the mixture was shielded from light and stirred overnight at 55° C. The reaction solution was concentrated under reduced pressure, water was added, and extraction was performed with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: toluene/ethyl acetate) to obtain the title compound (1.30 g, 49% yield).

Workup

  1. additionwas added
  2. stirringstirred overnight at 55° C
  3. concentrationThe reaction solution was concentrated under reduced pressure, water
  4. additionwas added
  5. extractionextraction
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (solvent: toluene/ethyl acetate)

Sources & evidence

ORD record
ord-2901784e9ad94bfbb138618a01e03662
Source dataset
uspto-grants-2007_09
Patent number
US07265108B2

Reaction notes

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