Potassium Carbonate → HCID 19974570, Verbindung

HRID 1451652Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1451652
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH2:21][NH:20][CH2:19][CH2:18]2.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH2:21][N:20]([CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1)[CH2:19][CH2:18]2

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 393566-Methoxy-1,2,3,4-tetrahydroisoquinolineHCID 792664-Nitrophenethyl bromide

Produkt 1

HCID 19974570HCID 19974570, VerbindungAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 1-(2-bromoethyl)-4-nitrobenzene (6.4 g), 1,2,3,4-tetrahydro-6-methoxyisoquinoline (4.6 g; Daniel J. Sall and Gary L. Grunewald, J. Med. Chem. 1987, 30, 2208-2216) and potassium carbonate (9.7 g) in DMF (150 ml) was stirred at 50° for 15 h. The mixture was evaporated to dryness and the residue was extracted with dichloromethane. The organic layer was washed with water, dried, filtered and evaporated. The residue was then purified by column chromatography eluting with dichloromethane/methanol (98:2) to give the title compound (2 g) as an oil which solidified on standing.

Aufarbeitung

  1. customThe mixture was evaporated to dryness
  2. extractionthe residue was extracted with dichloromethane
  3. washThe organic layer was washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was then purified by column chromatography
  8. washeluting with dichloromethane/methanol (98:2)

Quellen und Nachweise

ORD-Eintrag
ord-0103514f1288428c8164c1aa03238f31
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05604237

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