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

HRID 266131

Reaktionsgleichung

Reaktionsgleichung von HRID 266131
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, 6N hydrochloric acid (30 ml) was added to the residue, and the mixture was washed with dichloromethane. The aqueous layer was neutralized with 2N sodium hydroxide, and extracted with dichloromethane. The dichloromethane layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated. The residual crystals were separated by filtration, and then 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, 6N hydrochloric acid (30 ml)
  2. additionwas added to the residue
  3. washthe 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. customThe residual crystals were separated by filtration
  9. customrecrystallized from dichloromethane-hexane

Quellen und Nachweise

ORD-Eintrag
ord-cca11ca634f94b93b1a5b714bb54b0f4
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05650410

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