Chloroform → 4-Amino-6,7-dimethoxy-2-(piperazin-1-yl)quinoline

HRID 542211

Reaktionsgleichung

Reaktionsgleichung von HRID 542211
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:16]2[CH2:21][CH2:20][N:19](CC3C=CC=CC=3)[CH2:18][CH2:17]2)[CH:3]=1.C(Cl)(Cl)Cl>C(O)C.[Pd]>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:16]2[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]2)[CH:3]=1

Komponenten

5

Edukt 2

HCID 6212ChloroformHCID 133599914-Amino-6,7-dimethoxy-2-(4-benzylpiperazin-1-yl)quinoline

Produkt 1

HCID 140689984-Amino-6,7-dimethoxy-2-(piperazin-1-yl)quinolineAusbeute 51,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

4-Amino-6,7-dimethoxy-2-(4-benzylpiperazin-1-yl)quinoline (6.2 g) in ethanol (300 ml) with 5% Pd/C catalyst was stirred at 50° under an atmosphere of hydrogen (50 p.s.i.) for 20 hours. The mixture was cooled, chloroform (100 ml) added and the solution filtered through "Solkafloc". The solid was washed with chloroform-methanol (1:1, 4×100 ml) and the combined filtrates evaporated in vacuo. The residue was partitioned between chloroform-sodium carbonate solution (10%), the organic layer removed, the aqueous phase saturated with salt and further extracted with chloroform. The combined organic extracts were washed with brine, dried (Na2SO4) and evaporated in vacuo to yield 4-amino-6,7-dimethoxy-2-(piperazin-1-yl)quinoline (2.42 g). Spectroscopy showed this product to be the same as that of Example 32.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. filtrationthe solution filtered through "Solkafloc"
  3. washThe solid was washed with chloroform-methanol (1:1, 4×100 ml)
  4. customthe combined filtrates evaporated in vacuo
  5. customThe residue was partitioned between chloroform-sodium carbonate solution (10%)
  6. customthe organic layer removed
  7. extractionthe aqueous phase saturated with salt and further extracted with chloroform
  8. washThe combined organic extracts were washed with brine
  9. dry with materialdried (Na2SO4)
  10. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6479889b16bc45df8345a373e0507f3d
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04656174

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