1-Bromo-2-Chloroethane → HCID 23363882, Verbindung

HRID 1081272

Reaktionsgleichung

Reaktionsgleichung von HRID 1081272
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[NH:14][C:13](=[O:20])[C:12]2=[O:21].Br[CH2:23][CH2:24][Cl:25]>CN(C=O)C>[Cl:25][CH2:24][CH2:23][N:14]1[C:15]2[C:11](=[CH:10][C:9]([O:8][CH3:7])=[C:17]([O:18][CH3:19])[CH:16]=2)[C:12](=[O:21])[C:13]1=[O:20]

Komponenten

5

Edukt 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 47391485,6-dimethoxy-2,3-dihydro-1H-indole-2,3-dione

Produkt 1

HCID 23363882HCID 23363882, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Anhydrous potassium carbonate (2.44 g) was added to a solution of 5,6-dimethoxy-1H-indole-2,3-dione (1.2 g) in dry DMF (5 ml). 2-Bromo-1-chloroethane (4.1 g) was added and the mixture was heated at 70° C. for 2 hours. The mixture was evaporated to dryness under reduced pressure and the residue was purified by flash chromatography on silica gel. The 1-(2-chloroethyl)-5,6-dimethoxy-1H-indole-2,3-dione thus obtained was dissolved in dry DMF (5 ml) and anhydrous potassium carbonate (2.44 g), potassium iodide (100 mg) and 1-(phenylmethyl)piperazine (3.06 g) were added. The mixture was stirred and heated at 70° C. for 2 hours and then evaporated to dryness under reduced pressure. The residue was purified by chromatography to yield a red oil which on treatment with ethanolic HCl afforded 5,6-dimethoxy-1-[2-[4-(phenylmethyl)-1-piperazinyl]ethyl]-1H-indole-2,3-dione dihydrochloride (33%), m.p. 205°-207° C. (dec.).

Aufarbeitung

  1. customThe mixture was evaporated to dryness under reduced pressure
  2. customthe residue was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-80dc03e70e0c4676ae16fdc3867da439
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05585378

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