Water → HCID 22678386, compound

HRID 1837744Notes

Reaction equation

HRID 1837744 reaction equation
[O:1]=[C:2]1[C:7]([CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][C:17]3[C:18](Cl)=[N:19][CH:20]=[CH:21][CH:22]=3)[CH2:11][CH2:10]2)=[CH:6][CH:5]=[CH:4][NH:3]1.[H-].[Na+].O.[CH3:27][O:28][CH2:29][CH2:30][OH:31]>>[O:1]=[C:2]1[C:7]([CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][C:17]3[C:18]([O:31][CH2:30][CH2:29][O:28][CH3:27])=[N:19][CH:20]=[CH:21][CH:22]=3)[CH2:11][CH2:10]2)=[CH:6][CH:5]=[CH:4][NH:3]1

Participants

5

Reactant 4

HCID 962WaterHCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 22678325HCID 22678325, compound

Product 1

HCID 22678386HCID 22678386, compound

Conditions

Temperature
150 °C

Procedure

183 mg of 1-[(2-oxo-1,2-dihydro-3-pyridinyl)methyl]-4-[2-(2-chloro-3-pyridyl)ethyl]piperidine obtained in Example 117 and 226 mg of oil-dispersed 60% sodium hydride were suspended in 3 ml of 2-methoxyethanol, and the mixture was stirred at 150° C. for 2 hours. Water was added to the reaction solution, and the mixture was extracted with dichloromethane. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified by NH form silica gel column chromatography (methanol:ethyl acetate=1:19), to give 135 mg of the title compound as colorless crystals.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe crude product was purified by NH
  6. customform silica gel column chromatography (methanol:ethyl acetate=1:19)

Sources & evidence

ORD record
ord-370e73d608ca4e108e075b34e02979ac
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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