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

HRID 606155Notes

Reaction equation

HRID 606155 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-benzylpiperidine-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-798e3ee0e9934913b53f732a79fb2511
Source dataset
uspto-grants-2011_03
Patent number
US07915274B2

Reaction notes

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