Acetic Acid → 2-Methoxy-4-piperazin-1-yl-quinoline

HRID 333926

Reaktionsgleichung

Reaktionsgleichung von HRID 333926
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](OC)[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.[C:20](O)(=[O:22])C>COCCCOCCCO>[CH3:20][O:22][C:4]1[CH:3]=[C:2]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 4837PiperazineHCID 2283484-Chloro-6-methoxyquinoline

Produkt 1

HCID 668358742-Methoxy-4-piperazin-1-yl-quinolineAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 669843-(3-Methoxypropoxy)-1-propanolLösungsmittel

Versuchsvorschrift

A mixture of 4-chloro-6-methoxyquinoline (0.97 g, 5 mmol), piperazine (4.3 g, 50 mmol) and glacial acetic acid (0.3 ml) was heated under reflux with stirring in dipropyleneglycolmonomethylether for 48 hours. The mixture was filtered, the filtrate was evaporated to dryness under reduced pressure and the raw product was purified by column chromatography on a silica column using ethyl acetate and methanol with the addition of 0.1% NH3 to yield 0.85 g of a brown solid (3.3 mmol, 66%). MS (ES) m/z=243.8 [M+H]+.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated to dryness under reduced pressure
  5. customthe raw product was purified by column chromatography on a silica column
  6. additionwith the addition of 0.1% NH3

Quellen und Nachweise

ORD-Eintrag
ord-0a32e3b91e724d319bc86de297094ebc
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883791B2

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