Reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1[CH:10]=[C:11]([O:20][CH3:21])[CH:12]=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[C:14]2[CH3:19].[CH2:22]([S:24]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)(=[O:26])=[O:25])[CH3:23]>ClCCl.O>[CH2:22]([S:24]([N:27]1[CH2:28][CH2:29][N:30]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]2[CH:10]=[C:11]([O:20][CH3:21])[CH:12]=[C:13]3[C:18]=2[N:17]=[CH:16][CH:15]=[C:14]3[CH3:19])[CH2:31][CH2:32]1)(=[O:26])=[O:25])[CH3:23]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 1.5 g. (0.0049 mole) of N-(6-chlorohexyl)-6-methoxy-4-methyl-8-quinolinamine and 2.7 g (0.015 mole) of 1-(ethylsulfonyl)-piperazine was heated at 130° for 50 min, allowed to cool and taken up in dichloromethane and water. The organic layer was washed again, dried, and concentrated to dryness in vacuo. The residue was chromatographed over 70 g of silica gel first with ethyl acetate and then with 2% methanol in ethyl acetate. The eluant containing product, Rf(silica--ethyl acetate)=0.05, was concentrated to dryness in vacuo. Recrystallization of the residue from 2-propanol afforded 1.5 g (68%) of the title compound, mp 72°-74°.
Workup
- additionA mixture of 1.5 g
- temperatureto cool
- washThe organic layer was washed again
- customdried
- concentrationconcentrated to dryness in vacuo
- customThe residue was chromatographed over 70 g of silica gel first with ethyl acetate
- additionThe eluant containing product, Rf(silica--ethyl acetate)=0.05
- concentrationwas concentrated to dryness in vacuo
- customRecrystallization of the residue from 2-propanol
Sources & evidence
- ORD record
- ord-6f7c61972ac14997be44619fa524bffa
- Source dataset
- uspto-grants-1987_04
- Patent number
- US04659708
Linked notes
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