Potassium Carbonate → 1-[(2-Methoxy-3-pyridinyl)methyl]-4-[(2-methoxyphenoxy)methyl]piperidine

HRID 1837759Notes

Reaction equation

HRID 1837759 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9]Cl)=[CH:7][CH:6]=[CH:5][N:4]=1.[CH3:11][O:12][C:13]1[CH:26]=[CH:25][CH:24]=[CH:23][C:14]=1[O:15][CH2:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:20]2[CH2:19][CH2:18][CH:17]([CH2:16][O:15][C:14]3[CH:23]=[CH:24][CH:25]=[CH:26][C:13]=3[O:12][CH3:11])[CH2:22][CH2:21]2)=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 149329453-(Chloromethyl)-2-methoxypyridineHCID 222480304-[(2-Methoxyphenoxy)methyl]piperidine

Product 1

HCID 226786621-[(2-Methoxy-3-pyridinyl)methyl]-4-[(2-methoxyphenoxy)methyl]piperidineYield 82.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

200 mg of 2-methoxy-3-(chloromethyl)pyridine, 380 mg of 4-[(2-methoxyphenoxy)methyl]piperidine and 235 mg of potassium carbonate were added in 10 ml of acetonitrile, and the mixture were stirred at room temperature for 3 hours 15 minutes. After filtering the reaction solution, the solvent was evaporated, and the crude product was purified by silica gel column chromatography (hexane:ethyl acetate=3:2), to give 359 mg of the title compound as a colorless oil.

Workup

  1. filtrationAfter filtering the reaction solution
  2. customthe solvent was evaporated
  3. customthe crude product was purified by silica gel column chromatography (hexane:ethyl acetate=3:2)

Sources & evidence

ORD record
ord-79159ad056fd416ea496c4c8c71d6e3b
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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