Pyridine → HCID 11608128, compound
Reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[O:19]1CC[CH2:21][CH2:20]1.C(Cl)(=O)C>O.C(OCC)(=O)C>[C:1]1([CH:7]2[CH2:8][CH2:9][N:10]([C:20](=[O:19])[CH3:21])[CH2:11][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A mixture of commercially available 4-phenylpiperidine (10 g, 62 mmol), pyridine (5.7 mL, 70.5 mmol), and tetrahydrofuran (80 mL) was stirred at 0° C. and a mixture of acetyl chloride (5 mL, 70.3 mmol) and tetrahydrofuran (20 mL) was dripped over 10 minutes. The mixture was stirred under nitrogen atmosphere at 25° C. for 14 hours. Ethyl acetate (100 mL) and water (100 mL) were added to the reaction liquid for separation. The aqueous layer was extracted with ethyl acetate (100 mL), then the organic layers were combined, and the resultant was washed with a saturated aqueous sodium bicarbonate solution (100 mL), water (100 mL), and then a saturated saline solution (50 mL). The organic layer was dried over anhydrous magnesium sulfate and then the solvent was evaporated to obtain the title compound (12.3 g, 98%).
Workup
- stirringThe mixture was stirred under nitrogen atmosphere at 25° C. for 14 hours
- extractionThe aqueous layer was extracted with ethyl acetate (100 mL)
- washthe resultant was washed with a saturated aqueous sodium bicarbonate solution (100 mL), water (100 mL)
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- customthe solvent was evaporated
Sources & evidence
- ORD record
- ord-ec4376d647d14ae7b11e60d9e5f0755c
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933099B2
Reaction notes
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