Nitrogen → N-(2-(Dimethylamino)ethyl)acridine-4-carboxamide

HRID 1873070

Reaktionsgleichung

Reaktionsgleichung von HRID 1873070
[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:4]([C:15]([O:17]C)=O)=[CH:3][CH:2]=1.[CH3:19][N:20]([CH3:24])[CH2:21][CH2:22][NH2:23].N#N>C(O)CC>[CH3:19][N:20]([CH3:24])[CH2:21][CH2:22][NH:23][C:15]([C:4]1[C:5]2[C:14](=[CH:13][C:12]3[C:7]([N:6]=2)=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:1]=[CH:2][CH:3]=1)=[O:17]

Komponenten

5

Edukt 3

HCID 947NitrogenHCID 66053N,N-DimethylethylenediamineHCID 11064418Methyl Acridine-4-carboxylate

Produkt 1

HCID 107805N-(2-(Dimethylamino)ethyl)acridine-4-carboxamideAusbeute 64,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 10311-PropanolLösungsmittel

Versuchsvorschrift

A solution of methyl acridine 4-carboxylate (1.83 g, 7.72 mmol) and N,N-dimethylethylenediamine (3.40 g, 38.6 mmol) in n-propanol (80 ml) was flushed with N2, and the mixture was heated at reflux for three days under N2. Solvent was then removed under reduced pressure, and the residue was partitioned between CH2Cl2 (100 ml) and 1M Na2CO3 (100 ml). The organic layer was evaporated and the residue chromatographed on alumina, eluting with CH2Cl2 /MeOH (199:1) to give N-[2-(dimethylamino)ethyl]acridine-4-carboxamide (DACA) (1.47 g, 61%), mp (dihydrochloride salt from MeOH/EtOAc) 162-165° C.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux for three days under N2
  3. customSolvent was then removed under reduced pressure
  4. customthe residue was partitioned between CH2Cl2 (100 ml) and 1M Na2CO3 (100 ml)
  5. customThe organic layer was evaporated
  6. customthe residue chromatographed on alumina
  7. washeluting with CH2Cl2 /MeOH (199:1)

Quellen und Nachweise

ORD-Eintrag
ord-1889ca2d54664babbbe07d2030c12d6d
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06111109

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