Piperazine → Ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-piperazinomethylquinoline-3-carboxylate

HRID 1458940Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1458940
Cl[CH2:2][C:3]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)[C:10]2[C:5](=[CH:6][C:7]([O:30][CH3:31])=[C:8]([O:28][CH3:29])[CH:9]=2)[N:4]=1.[NH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>CO>[CH3:27][O:26][C:20]1[CH:19]=[C:18]([C:11]2[C:10]3[C:5](=[CH:6][C:7]([O:30][CH3:31])=[C:8]([O:28][CH3:29])[CH:9]=3)[N:4]=[C:3]([CH2:2][N:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[C:12]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:23]=[CH:22][C:21]=1[O:24][CH3:25]

Komponenten

4

Edukt 2

HCID 4837PiperazineHCID 10813243Ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate

Produkt 1

HCID 22097621Ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-piperazinomethylquinoline-3-carboxylateAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate (1.0 g), piperazine (1.15 g) and methanol (15 ml) was stirred at room temperature for 36 hours. The reaction mixture was concentrated under reduced pressure, and 6N HCl (30 ml) was added to the residue. The resulting mixture was washed with dichloromethane. The aqueous layer was neutralized with 2N NaOH and extracted with dichloromethane. The dichloromethane layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated. The crystals were collected by filtration and recrystallized from dichloromethane-hexane to give ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-piperazinomethylquinoline-3-carboxylate (0.43 g, 39%). Colorless prisms. mp. 192°-193° C.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and 6N HCl (30 ml)
  2. additionwas added to the residue
  3. washThe resulting mixture was washed with dichloromethane
  4. extractionextracted with dichloromethane
  5. washThe dichloromethane layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent was evaporated
  8. filtrationThe crystals were collected by filtration
  9. customrecrystallized from dichloromethane-hexane

Quellen und Nachweise

ORD-Eintrag
ord-887ccc8180c148eea429d3e6857cb3e2
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05852039

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