Potassium Carbonate → HCID 86713220, compound
Reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:10][CH3:11])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>CN(C)C=O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH3:11][O:10][C:4]1[CH:3]=[C:2]([O:1][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 100 °C
Procedure
In 2.0 mL of N,N-dimethylformamide were dissolved 304 mg (2.00 mmol) of 4-hydroxy-2-methoxybenzaldehyde, 0.55 g (4.0 mmol) of potassium carbonate, and 64 mg (0.20 mmol) of tetrabutylammonium bromide. To this solution was added 0.74 g (4.0 mmol) of 1-(2-chloroethyl)piperidine hydrochloride and the mixture was stirred at 100° C. overnight. The resulting reaction mixture was diluted with ethyl acetate (100 mL), washed with water and then with saturated brine (each in an amount of 20 mL), and dried over magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0 to 90/10) to give 88.9 mg (16% yield) of the title compound as a brown viscous matter.
Workup
- customThe resulting reaction mixture
- washwashed with water
- dry with materialwith saturated brine (each in an amount of 20 mL), and dried over magnesium sulfate
- filtrationAfter filtration
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0 to 90/10)
Sources & evidence
- ORD record
- ord-d896e45d016f4ca38683f27d53c2aa48
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09399635B2
Reaction notes
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