Potassium Carbonate → Methyl 1-benzylpiperidine-4-carboximidate
Reaction equation
Cl.Cl.[CH2:3]([N:10]1[CH2:15][CH2:14][CH:13]([C:16](=[NH:19])[O:17][CH3:18])[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[CH2:3]([N:10]1[CH2:11][CH2:12][CH:13]([C:16](=[NH:19])[O:17][CH3:18])[CH2:14][CH2:15]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
6.1 g of methyl 1-benzylpiperidine-4-carboximidate dihydrochloride was distributed into an aqueous solution of potassium carbonate and ethyl acetate under ice-cooling. The organic layer was extracted and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, 4.7 g of free methyl 1-benzylpiperidine-4-carboximidate was obtained as a colorless oily substance. A solution of 2.35 g of methyl 1-benzylpiperidine-4-carboximidate and 0.95 g (10 mmol) of methanesulfonamide in dry methanol was stirred at room temperature for 3 days. Subsequently, 1.0 g of palladium-carbon was added to the reaction mixture and the resulting mixture was stirred in a hydrogen atmosphere under atmospheric pressure for 1 hour. The inorganic matters were eliminated by filtering through celite. After distilling off the solvent under reduced pressure, the residue was recrystallized from methanol to thereby give 1.38 g of the title compound as colorless needles.
Workup
- temperaturecooling
- extractionThe organic layer was extracted
- dry with materialdried over anhydrous sodium sulfate
- distillationAfter distilling off the solvent under reduced pressure
Sources & evidence
- ORD record
- ord-9802986a210a4a148a1c2f7d65882414
- Source dataset
- uspto-grants-2003_02
- Patent number
- US06518423B1
Reaction notes
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