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

HRID 890063Notes

Reaction equation

HRID 890063 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 saws 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 fleas 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 fleas purified by silica gel column chromatography (solvent: toluene/ethyl acetate)

Sources & evidence

ORD record
ord-7862c342fff74a95a0143a3ad6ea054d
Source dataset
uspto-grants-2006_02
Patent number
US06995144B2

Reaction notes

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