Reaktion #353313

Reaktionsgleichung

ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate

piperazine

→

ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-piperazinomethylquinoline-3-carboxylate

Ausbeute 39.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated under reduced pressure, 6N hydrochloric acid (30 ml)
2. 2
   workup.ADDITIONwas added to the residue
3. 3
   Waschenthe mixture was washed with dichloromethane
4. 4
   Extraktionextracted with dichloromethane
5. 5
   WaschenThe dichloromethane layer was washed with water
6. 6
   Trocknendried over magnesium sulfate
7. 7
   Sonstigethe solvent was evaporated
8. 8
   SonstigeThe residual crystals were separated by filtration
9. 9
   Sonstigerecrystallized from dichloromethane-hexane

Vorschrift

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.

Quelle