1-Piperazinecarboxylic acid, ethyl ester → 4-[6-[[6-Methoxy-4-methyl-8-quinolinyl]amino]hexyl]-1-piperazinecarboxylic

HRID 542846

Reaktionsgleichung

Reaktionsgleichung von HRID 542846
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1[CH:10]=[C:11]([O:20][CH3:21])[CH:12]=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[C:14]2[CH3:19].[N:22]1([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:21][O:20][C:11]1[CH:12]=[C:13]2[C:18](=[C:9]([NH:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:25]3[CH2:24][CH2:23][N:22]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:27][CH2:26]3)[CH:10]=1)[N:17]=[CH:16][CH:15]=[C:14]2[CH3:19]

Komponenten

5

Edukt 2

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 608631N-[6-Chlorohexyl]-6-methoxy-4-methyl-8-quinolinamine

Produkt 1

HCID 6346964-[6-[[6-Methoxy-4-methyl-8-quinolinyl]amino]hexyl]-1-piperazinecarboxylicAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 6.0 g (0.0195 mole) of N-(6-chlorohexyl)-6-methoxy-4-methyl-8-quinolinamine and 6 ml of 1-piperazinecarboxylic acid, ethyl ester in 2 ml of toluene was heated in an oil bath at 135° for 3 hr, allowed to cool, diluted with ethyl acetate and toluene, washed with water, dried, and concentrated to dryness in vacuo. The residue was chromatographed over 700 g of silica gel first with 2 l of ethyl acetate and then with 2 l each of the following solutions of methanol in ethyl acetate: 2%, 5%, 10%, and 20%. The eluant containing product, Rf (silica--ethyl acetate)=0.16, was concentrated to dryness. The residue was taken up in ether, filtered to remove dark flocculent material, and then treated with 1.2 ml of 85% phosphoric acid in 30 ml of ethanol. The gum which settled was washed with ether and acetone and then dissolved in 2-propanol and water. The pH of the solution was adjusted to 8 with ammonium hydroxide. The solution was then heated on the steambath, diluted with water to the cloud point and chilled to afford 1.7 g (21%) of the title compound, mp. 59°-60°.

Aufarbeitung

  1. temperaturewas heated in an oil bath at 135° for 3 hr
  2. temperatureto cool
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated to dryness in vacuo
  6. customThe residue was chromatographed over 700 g of silica gel first with 2 l of ethyl acetate
  7. additionThe eluant containing product, Rf (silica--ethyl acetate)=0.16
  8. concentrationwas concentrated to dryness
  9. filtrationfiltered
  10. customto remove dark flocculent material
  11. additiontreated with 1.2 ml of 85% phosphoric acid in 30 ml of ethanol
  12. washThe gum which settled was washed with ether and acetone
  13. dissolutiondissolved in 2-propanol
  14. temperatureThe solution was then heated on the steambath
  15. additiondiluted with water to the cloud point
  16. temperaturechilled

Quellen und Nachweise

ORD-Eintrag
ord-445fe5b8fbc745369130cb561f67326b
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04659708

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