Hydrochloric Acid → 1-[(2-Oxo-1,2-dihydro-3-pyridinyl)methyl]-4-[2-(2-methylsulfonylaminophenyl)-2-oxoethyl]piperidine

HRID 1837748Notes

Reaction equation

HRID 1837748 reaction equation
C[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:26]([CH3:29])(=[O:28])=[O:27])=[O:18])[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][N:4]=1.Cl>C(#N)C>[O:2]=[C:3]1[C:8]([CH2:9][N:10]2[CH2:11][CH2:12][CH:13]([CH2:16][C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[O:18])[CH2:14][CH2:15]2)=[CH:7][CH:6]=[CH:5][NH:4]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 226783911-[(2-Methoxy-3-pyridyl)methyl]-4-[2-(2-methylsulfonylaminophenyl)-2-oxoethyl]piperidine

Product 1

HCID 226783001-[(2-Oxo-1,2-dihydro-3-pyridinyl)methyl]-4-[2-(2-methylsulfonylaminophenyl)-2-oxoethyl]piperidineYield 51.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In acetonitrile (4 ml) were dissolved 90 mg of 1-[(2-methoxy-3-pyridyl)methyl]-4-[2-(2-methanesulfonylaminophenyl)-2-oxoethyl]piperidine obtained in Example 65 and 0.30 ml of concentrated hydrochloric acid, followed by heating under reflux for 5 hours. The solvent was evaporated, and then the residue was dissolved in ethyl acetate and an aqueous 1N sodium hydroxide. The organic layer was separated, washed with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was recrystallized from ethanol, to give 45 mg of the title compound as colorless crystals.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 5 hours
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated
  9. customthe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-3209161db6834257a7466943a4a72ec1
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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