Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:4][CH:3]=1.[H-].[K+].Br[CH2:19][CH:20]=[CH:21][CH3:22]>O1CCCC1>[CH2:19]([N:9]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH:20]=[CH:21][CH3:22]Participants
Procedure
A solution of 4.4 g of N-[(4-chlorophenyl)methyl]-(3-pyridyl)amine dissolved in 50 ml of tetrahydrofuran was added to a suspension of 4 g of a 24.6% suspension of potassium hydride in oil in tetrahydrofuran. The mixture was allowed to stir at room temperature for approximately 30 minutes whereupon 4 g of 1-bromo-2-butene was added dropwise to the reaction mixture. The mixture was allowed to stir at room temperature overnight at which time the solution was evaporated to dryness. The residue was dissolved in dichloromethane and washed with water. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum. The oil residue was chromatographed over silica gel. Fractions containing the major component were combined and the solvent was evaporated therefrom to provide 3 g of N-(2-butenyl)-N-[(4-chlorophenyl)methyl]-(3-pyridyl)amine as an oil.
Workup
- additionwas added dropwise to the reaction mixture
- customwas evaporated to dryness
- dissolutionThe residue was dissolved in dichloromethane
- washwashed with water
- dry with materialThe organic phase was dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum
- customThe oil residue was chromatographed over silica gel
- additionFractions containing the major component
- customthe solvent was evaporated
Sources & evidence
- ORD record
- ord-c8d0fcc40cb94070ab4cc37bf1690e53
- Source dataset
- uspto-grants-1985_11
- Patent number
- US04552960
Linked notes
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