Triethylamine → 1-[(2-Methoxy-3-pyridyl)methyl]-4-[2-(2-methylsulfonylaminophenyl)-2-oxoethyl]piperidine

HRID 1837739Notes

Reaction equation

HRID 1837739 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[NH2:25])=[O:18])[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][N:4]=1.C(N(CC)CC)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[NH:25][S:34]([CH3:33])(=[O:36])=[O:35])=[O:18])[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 226784371-[(2-Methoxy-3-pyridyl)methyl]-4-[2-(2-aminophenyl)-2-oxoethyl]piperidine

Product 1

HCID 226783911-[(2-Methoxy-3-pyridyl)methyl]-4-[2-(2-methylsulfonylaminophenyl)-2-oxoethyl]piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

120 mg of 1-[(2-methoxy-3-pyridyl)methyl]-4-[2-(2-aminophenyl)-2-oxoethyl]piperidine obtained in Example 64, 0.1 ml of triethylamine and 0.041 ml of methanesulfonyl chloride were dissolved in 2 ml of dichloromethane, and the mixture was stirred for 2 hours under ice-cooling. An aqueous sodium bicarbonate was added to the reaction solution, and the mixture was extracted with ethyl acetate. 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 silica gel column chromatography (ethyl acetate), to give 90 mg of the title compound as a yellow oil.

Workup

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

Sources & evidence

ORD record
ord-8ef781a9095b48c6aec3c01979c9ade3
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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