Acetonitrile → HCID 22678365, compound

HRID 1837761Notes

Reaction equation

HRID 1837761 reaction equation
C(#N)C.[CH3:4][O:5][C:6]1[C:11]([CH2:12]Cl)=[CH:10][CH:9]=[CH:8][N:7]=1.[CH2:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[CH2:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1/[CH:28]=[CH:29]/[CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[CH3:4][O:5][C:6]1[C:11]([CH2:12][N:33]2[CH2:34][CH2:35][CH:30](/[CH:29]=[CH:28]/[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[O:21][CH2:20][CH:15]3[CH2:14][CH2:19][CH2:18][CH2:17][CH2:16]3)[CH2:31][CH2:32]2)=[CH:10][CH:9]=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 149329453-(Chloromethyl)-2-methoxypyridineHCID 22248046HCID 22248046, compound

Product 1

HCID 22678365HCID 22678365, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To acetonitrile (10 ml) were added 500 mg of 2-methoxy-3-(chloromethyl)pyridine, 1.04 g of 4-[(E)-2-[(2-cyclohexylmethyloxy)phenyl]-1-ethenyl]piperidine and 531 mg of potassium carbonate, followed by stirring at room temperature overnight. Ethyl acetate was added to the reaction solution, and the mixture was filtered through alumina-silica gel. Then, the solvent was evaporated, and the crude product was purified by silica gel column chromatography (hexane:ethyl acetate=8:1), to give 961 mg of the title compound as a pale yellow oil.

Workup

  1. filtrationthe mixture was filtered through alumina-silica gel
  2. customThen, the solvent was evaporated
  3. customthe crude product was purified by silica gel column chromatography (hexane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-2c80c5db09ec4a298ae0e24f10b33575
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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