Water → 1-(1-Benzylpiperidin-4-yl)-2-(2-methoxyphenyl)ethanone

HRID 890021Notes

Reaction equation

HRID 890021 reaction equation
[CH:1](=O)[C:2]1[C:3]([O:8][CH3:9])=[CH:4][CH:5]=[CH:6][CH:7]=1.C[O-].[K+].[CH2:14]([N:21]1[CH2:26][CH2:25][CH:24]([CH:27]=[O:28])[CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CO.C(OCC)(=O)C>[CH2:14]([N:21]1[CH2:26][CH2:25][CH:24]([C:27](=[O:28])[CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[O:8][CH3:9])[CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 86582-MethoxybenzaldehydeHCID 895841-Benzylpiperidine-4-carbaldehydeHCID 23664618Potassium methoxide

Product 1

HCID 222480731-(1-Benzylpiperidin-4-yl)-2-(2-methoxyphenyl)ethanoneYield 16%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

After dissolving 1.34 g of o-anisaldehyde in 10 ml of methanol, 1.83 g of p-toluenesulfonyl hydrazide was added, the mixture was stirred for 2 hours at room temperature and then 725 mg of potassium methoxide and a solution of 1.00 g of 1-benylpiperidine-4-carboxaldehyde in methanol (3 ml) was added, and the mixture was shielded from light and stirred overnight at 55° C. Water was added to the reaction solution, 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 (249 mg, 16% yield).

Workup

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

Sources & evidence

ORD record
ord-9d49d278160443e6b6335c8e2d05033c
Source dataset
uspto-grants-2006_02
Patent number
US06995144B2

Reaction notes

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