Water → Methyl 1-[5-(trifluoromethyl)pyridin-2-yl]piperidine-4-carboxylate
Reaction equation
CI.[F:3][C:4]([F:21])([F:20])[C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=[O:18])[CH2:13][CH2:12]2)=[N:9][CH:10]=1.[C:22](=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[F:21][C:4]([F:3])([F:20])[C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]([O:19][CH3:22])=[O:18])[CH2:13][CH2:12]2)=[N:9][CH:10]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Methyl iodide (0.30 mL, 4.82 mmol) was added to a solution of 1-[5-(trifluoromethyl)pyridin-2-yl]piperidine-4-carboxylic acid (1.00 g, 3.65 mmol) and potassium carbonate (800 mg, 5.79 mmol) in DMF (10 mL), and the mixture was stirred at room temperature for 6 hours. Water was added to the reaction solution, followed by extraction with diethyl ether twice. The obtained organic layer was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate=100/0-60/40 (gradient)] to obtain the title compound (1.03 g, yield: 98%).
Workup
- extractionfollowed by extraction with diethyl ether twice
- washThe obtained organic layer was washed with brine
- dry with materialdried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate=100/0-60/40 (gradient)]
Sources & evidence
- ORD record
- ord-edbe95c214074eb5b2b7322913d2c43a
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150575B2
Reaction notes
Loading…