Hydrogen chloride-ethyl acetate → 1-[(2-Oxo-1,2-dihydro-3-pyridinyl)methyl]-4-[2-(2-methylphenyl)ethyl]piperidine
Reaction equation
C[O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH3:24])[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][N:4]=1.C(OCC)(=O)C.Cl>C(O)C>[O:2]=[C:3]1[C:8]([CH2:9][N:10]2[CH2:11][CH2:12][CH:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH3:24])[CH2:14][CH2:15]2)=[CH:7][CH:6]=[CH:5][NH:4]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
In ethanol (10 ml) was dissolved 465 mg of 1-[(2-methoxy-3-pyridyl)methyl]-4-[2-(2-methylphenyl)ethyl]piperidine. To the mixture was added 1.75 ml of a 4N-hydrogen chloride-ethyl acetate solution, followed by heating under reflux for 3 hours. The solvent was evaporated, an aqueous sodium bicarbonate was added to the residue, and the mixture was extracted with chloroform. The extract was dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The resulting solid was recrystallized from ethyl acetate, to give 344 mg of the title compound as white needles.
Workup
- temperatureby heating
- temperatureunder reflux for 3 hours
- customThe solvent was evaporated
- additionan aqueous sodium bicarbonate was added to the residue
- extractionthe mixture was extracted with chloroform
- dry with materialThe extract was dried over anhydrous magnesium sulfate
- customthe solvent was evaporated
- customThe resulting solid was recrystallized from ethyl acetate
Sources & evidence
- ORD record
- ord-9ceacd18145747e38b87f5a2e8e0a001
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06784192B2
Reaction notes
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