Potassium Carbonate → Ethyl 4-(4-hydroxypiperidin-1-yl)benzoate
Reaction equation
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[OH:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[OH:13][CH:14]1[CH2:19][CH2:18][N:17]([C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)[CH2:16][CH2:15]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
To a 20 ml N,N-dimethylformamide solution of 1.0 g (5.95 mmol) of ethyl 4-fluorobenzoate, 662 mg (6.54 mmol) of 4-hydroxypiperidine and 1.23 g (8.92 mmol) of potassium carbonate were added, and the mixture was stirred for 24 hours at 120° C. The reaction mixture was returned to room temperature, and the solvent was distilled off under reduced pressure. Then, water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and dried over sodium sulfate. Then, the solvent was distilled off under reduced pressure. Diethyl ether was added to the residue, and precipitated crystals were collected to obtain 234 mg (16%) of the captioned compound.
Workup
- customwas returned to room temperature
- distillationthe solvent was distilled off under reduced pressure
- additionThen, water was added to the residue
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with a saturated aqueous solution of sodium chloride
- dry with materialdried over sodium sulfate
- distillationThen, the solvent was distilled off under reduced pressure
- additionDiethyl ether was added to the residue
- customprecipitated crystals
- customwere collected
Sources & evidence
- ORD record
- ord-8dda63a76a6449e69d90e8363ae5f7b7
- Source dataset
- uspto-grants-2007_09
- Patent number
- US07268128B2
Reaction notes
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