Potassium Carbonate → 3-{[3-(dimethylamino)propyl]amino}-N,N-bis(3-methylbutyl)-4-nitrobenzamide

HRID 899911Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 899911
F[C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[N+:21]([O-:23])=[O:22])[C:5]([N:7]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[O:6].[CH2:24]([N:26]([CH2:31]C)[CH2:27][CH2:28][CH2:29][NH2:30])C.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:24][N:26]([CH3:31])[CH2:27][CH2:28][CH2:29][NH:30][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[N+:21]([O-:23])=[O:22])[C:5]([N:7]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[O:6]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 61011N,N-Diethyl-1,3-propanediamineHCID 684471113-fluoro-N,N-bis(3-methylbutyl)-4-nitrobenzamide

Produkt 1

HCID 687903453-{[3-(dimethylamino)propyl]amino}-N,N-bis(3-methylbutyl)-4-nitrobenzamideAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 3-fluoro-N,N-bis(3-methylbutyl)-4-nitrobenzamide (2.5 g, 1 eq, prepared according to Example A1), 3-diethylamino-propylamine (877 mg, 1.1 eq) and potassium carbonate (2.13 g, 2 eq) in acetonitrile (80 ml) is heated under reflux for 5 hours then concentrated under reduced pressure at 40° C. The residue is taken up in dichloromethane (130 ml) and water (50 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 by flash chromatography on silica gel (eluent: dichloromethane/methanol 9:1) produces the expected compound in the form of a yellow oil (2.1 g mg; 68% yield).

Aufarbeitung

  1. temperatureis heated
  2. temperatureunder reflux for 5 hours
  3. concentrationthen concentrated 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 by flash chromatography on silica gel (eluent: dichloromethane/methanol 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-92dd63bd94a34bce802ff94e735bac32
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07355052B2

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