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Dibutylamine → N6,N6-dibutyl-3-nitro-N2-(3-piperidin-1-ylpropyl)pyridine-2,6-diamine

HRID 1727036
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1727036
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([NH:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:8][CH2:9][CH3:10].Cl[C:17]1[N:22]=[C:21]([NH:23][CH2:24][CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[C:20]([N+:33]([O-:35])=[O:34])=[CH:19][CH:18]=1>C(#N)C>[CH2:7]([N:11]([CH2:12][CH2:13][CH2:14][CH3:15])[C:17]1[N:22]=[C:21]([NH:23][CH2:24][CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[C:20]([N+:33]([O-:35])=[O:34])=[CH:19][CH:18]=1)[CH2:8][CH2:9][CH3:10]
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Komponenten

5

Edukt 3

HCID 8148DibutylamineHCID 11430Potassium CarbonateHCID 860008436-chloro-3-nitro-N-(3-piperidin-1-ylpropyl)pyridin-2-amine

Produkt 1

HCID 86000846N6,N6-dibutyl-3-nitro-N2-(3-piperidin-1-ylpropyl)pyridine-2,6-diamineAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel
2×

Versuchsvorschrift

Potassium carbonate (54 mg, 2 eq) and a solution of dibutylamine (30 mg, 1.2 eq) in acetonitrile (2 ml) are added successively to a solution of 6-chloro-3-nitro-N-(3-piperidin-1-ylpropyl)pyridin-2-amine (59 mg, 1 eq) in acetonitrile (3 ml). The mixture is heated to reflux for 15 hours then cooled down to ambient temperature and concentrated under reduced pressure at 40° C. The residue is taken up in dichloromethane (200 ml) and water (90 ml). After decantation and extractions, the combined organic phases are washed with salt water, dried over Na2SO4 then concentrated under reduced pressure at 40° C. Purification of the residue obtained, by flash chromatography on silica gel (eluent: heptane/ethyl acetate 1:1 to 100% ethyl acetate), produces the expected compound (73 mg; 95% yield).

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 15 hours
  3. concentrationconcentrated under reduced pressure at 40° C
  4. extractionAfter decantation and extractions
  5. washthe combined organic phases are washed with salt water
  6. dry with materialdried over Na2SO4
  7. concentrationthen concentrated under reduced pressure at 40° C
  8. customPurification of the residue
  9. customobtained, by flash chromatography on silica gel (eluent: heptane/ethyl acetate 1:1 to 100% ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-d1a2709a203244a1a1d59758a017f006
Quelldatensatz
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07495009B2

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