Chloroform → 4-amino-6,7-dimethoxy-2-[4-(N-phenylcarbamoyl)piperazin-1-yl]quinoline dihydrochloride

HRID 845413

Reaktionsgleichung

Reaktionsgleichung von HRID 845413
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:10][C:11]1[C:20]2[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=2)[N:14]=[C:13]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:12]=1.C(Cl)(Cl)[Cl:32]>>[ClH:32].[ClH:32].[NH2:10][C:11]1[C:20]2[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=2)[N:14]=[C:13]([N:25]2[CH2:26][CH2:27][N:28]([C:8](=[O:9])[NH:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:29][CH2:30]2)[CH:12]=1

Komponenten

4

Edukt 3

HCID 6212ChloroformHCID 7672Phenyl isocyanateHCID 140689984-Amino-6,7-dimethoxy-2-(piperazin-1-yl)quinoline

Produkt 1

HCID 201311314-amino-6,7-dimethoxy-2-[4-(N-phenylcarbamoyl)piperazin-1-yl]quinoline dihydrochloride

Versuchsvorschrift

Phenylisocyanate (1.1 g) was added to a stirred suspension of 4-amino-6,7-dimethoxy-2-(piperazin-1-yl)quinoline (0.72 g) in chloroform (25 ml) a room temperature and the reaction mixture was stirred for 4 hours. The mixture was evaporated in vacuo, the residue taken up in methanol-chloroform and treated with ethereal hydrogen chloride. The crude product was purified by chromatography on silica gel eluting with methylene chloride followed by chloroform/methanol and then recrystallised from methanol/ether to give 4-amino-6,7-dimethoxy-2-[4-(N-phenylcarbamoyl)piperazin-1-yl]quinoline dihydrochloride (0.18 g), m.p. 235°.

Aufarbeitung

  1. customThe mixture was evaporated in vacuo
  2. additiontreated with ethereal hydrogen chloride
  3. customThe crude product was purified by chromatography on silica gel eluting with methylene chloride
  4. customrecrystallised from methanol/ether

Quellen und Nachweise

ORD-Eintrag
ord-7c57e5701076476490997332b4bee357
Quelldatensatz
uspto-grants-1988_07
Patentnummer
US04758568

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