Morpholine → 5-(4-Morpholinylmethyl)-8-quinolinol

HRID 23939Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 23939
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[CH2:8][C:9]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]2[C:10]=1[CH:11]=[CH:12][CH:13]=[N:14]2>C(Cl)(Cl)Cl>[O:4]1[CH2:5][CH2:6][N:1]([CH2:8][C:9]2[CH:18]=[CH:17][C:16]([OH:19])=[C:15]3[C:10]=2[CH:11]=[CH:12][CH:13]=[N:14]3)[CH2:2][CH2:3]1

Komponenten

4

Edukt 2

HCID 8083MorpholineHCID 4168815-(Chloromethyl)quinolin-8-ol

Produkt 1

HCID 10903035-(4-Morpholinylmethyl)-8-quinolinolAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

Morpholine (1.9 ml; 21.8 mmol) was added to a solution of 5-chloromethyl-8-hydroxyquinoline (1.98 g; 8.34 mmol) in CHCl3 (50 ml) at 5° C. The reaction mixture was stirred overnight at room temperature. Then CHCl3 (100 ml) was added and the solution was washed with 5% NaHCO3 (2×50 ml), followed by brine (50 ml), and dried over Na2SO4. The solution was filtered and evaporated under vacuum to dryness. The residue was crystallized from hexane-CHCl3 and gave 1.2 g (59%) of the title product. M.p. 130° C. TLC (CHCl3; MeOH; NH3=8:2:0.5. Rf=0.69.

Aufarbeitung

  1. washthe solution was washed with 5% NaHCO3 (2×50 ml)
  2. dry with materialdried over Na2SO4
  3. filtrationThe solution was filtered
  4. customevaporated under vacuum to dryness
  5. customThe residue was crystallized from hexane-CHCl3

Quellen und Nachweise

ORD-Eintrag
ord-d327b4f511f44069aecb5e4b9549be84
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855711B1

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