1,2,3,4-Tetrahydroisoquinoline → 1,2,3,4-Tetrahydro-2-[3-(4-nitrophenoxy)propyl]isoquinoline

HRID 1451656Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1451656
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1.[CH2:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][CH2:17][NH:16]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N+:12]([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:16]2[CH2:17][CH2:18][C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15]2)=[CH:7][CH:8]=1)([O-:14])=[O:13]

Komponenten

5

Edukt 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 11430Potassium CarbonateHCID 2611281-(3-Bromopropoxy)-4-nitrobenzene

Produkt 1

HCID 103808031,2,3,4-Tetrahydro-2-[3-(4-nitrophenoxy)propyl]isoquinolineAusbeute 73,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 1-(3-bromopropoxy)-4-nitrobenzene (10 g), 1,2,3,4-tetrahydroisoquinoline (5.1 g) and potassium carbonate (10.6 g) in DMF (100 ml) was stirred at 70° for 24 h. The mixture was then filtered and the filtrate evaporated. The residue was taken up with water and extracted with dichloromethane. The organic layer was washed with water, dried, evaporated and purified by column chromatography eluting with dichloromethane/methanol (96:4) to give the title compound (8.8 g) as a yellow oil. NMR includes signals at d 3.6 (2H,s,N--CH2Ar), 4.1 (2H,t,O--CH2).

Aufarbeitung

  1. filtrationThe mixture was then filtered
  2. customthe filtrate evaporated
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with water
  5. customdried
  6. customevaporated
  7. custompurified by column chromatography
  8. washeluting with dichloromethane/methanol (96:4)

Quellen und Nachweise

ORD-Eintrag
ord-34d0f8ace30a4d25bf0afd0adcc6e962
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05604237

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