Dibenamine hydrochloride → 9-(2-Dibenzylamino-ethoxy)-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid 2-dibenzylamino-ethyl ester

HRID 2099122

Reaktionsgleichung

Reaktionsgleichung von HRID 2099122
[OH:1][C:2]1[CH:3]=[C:4]2[C:9]3=[C:10]([CH2:12][CH2:13][CH2:14][N:8]3[CH:7]=[C:6]([C:15]([OH:17])=[O:16])[C:5]2=[O:18])[CH:11]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[CH2:26]([N:33]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:34][CH2:35]Cl)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C>[CH2:26]([N:33]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:34][CH2:35][O:16][C:15]([C:6]1[C:5](=[O:18])[C:4]2[C:9]3=[C:10]([CH2:12][CH2:13][CH2:14][N:8]3[CH:7]=1)[CH:11]=[C:2]([O:1][CH2:35][CH2:34][N:33]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH:3]=2)=[O:17])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Komponenten

5

Edukt 3

HCID 5925Dibenamine hydrochloride2×HCID 11430Potassium Carbonate2×HCID 214453649-Hydroxy-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid

Produkt 1

HCID 688610139-(2-Dibenzylamino-ethoxy)-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid 2-dibenzylamino-ethyl esterAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

9-Hydroxy-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid (GB1417129) (0.905 g, 3.69 mmol) was suspended in dry DMF (50 mL). To this was added potassium carbonate (3.06 g, 22 mmol) and dibenzyl-(2-chloroethyl)amine hydrochloride (2.37 g, 8 mmol). The mixture was heated at 60° C. for 16 h, then more potassium carbonate (0.55 g) and dibenzyl-(2-chloroethyl)amine hydrochloride (1.18 g, 4 mmol) were added. After a further 25 h at 75° C. the mixture was evaporated. The residue was diluted with water and extracted with ethyl acetate (×3). The combined organic extracts were washed with brine, dried and evaporated under reduced pressure. The crude product (4.0 g) was purified by chromatography on silica gel (100 g), eluting with 0-4% methanol in dichloromethane, to give the title compound (2.25 g, 89%); ESMS m/z 692 [M+H]+ (100%).

Aufarbeitung

  1. customAfter a further 25 h at 75° C. the mixture was evaporated
  2. additionThe residue was diluted with water
  3. extractionextracted with ethyl acetate (×3)
  4. washThe combined organic extracts were washed with brine
  5. customdried
  6. customevaporated under reduced pressure
  7. customThe crude product (4.0 g) was purified by chromatography on silica gel (100 g)
  8. washeluting with 0-4% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-5b3f986604304e2ea9dde706c43d7720
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07569550B2

Verknüpfte Notizen

Wird geladen…