Reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH3:10].COCCCOCCCO.[NH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.CN(C)C1C=CC=CC=1>>[CH3:10][O:9][C:3]1[C:4]([CH3:8])=[N:5][CH:6]=[CH:7][C:2]=1[N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1Participants
Conditions
- Temperature
- 140 °C
Procedure
4-Chloro-3-methoxy-2-methyl-pyridine (0.47 g, 3 mmol) was mixed with dipropyleneglycolmonomethylether (3 ml), piperazine (1.1 g, 7.2 mmol) and N,N-dimethylaniline (0.36 g, 3 mmol) and stirred at 140° C. for 72 hours. The solvent was removed under reduced pressure and the residue was purified by column chromatography (prepacked silica column, gradient ethyl acetate/methanol with the addition of 1% ammonia). The raw product was dissolved in 1M NaOH and extracted with a mixture of diethylether, dichloromethane and ethylacetate (1:1:1) several times. The combined organic phases were washed with water, dried over sodium sulfate, and the solvent was removed under reduced pressure to yield 585 mg of a yellow solid (2.8 g, 94%). MS (APCI): m/z=208.0 [M+1]+.
Workup
- customThe solvent was removed under reduced pressure
- customthe residue was purified by column chromatography (prepacked silica column, gradient ethyl acetate/methanol
- additionwith the addition of 1% ammonia)
- dissolutionThe raw product was dissolved in 1M NaOH
- extractionextracted with a mixture of diethylether, dichloromethane and ethylacetate (1:1:1) several times
- washThe combined organic phases were washed with water
- dry with materialdried over sodium sulfate
- customthe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-fd595ac2c5bc423eb5643a5e9bd250f5
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08883791B2
Linked notes
Loading…