1,2,3,4-Tetrahydroquinoline → 1-[(4-Pyridin-3-yl-8-azabicyclo[3.2.1]oct-8-yl)carbonyl]-1,2,3,4-tetrahydroquinoline

HRID 599354Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 599354
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.ClC(Cl)(O[C:15](=[O:21])OC(Cl)(Cl)Cl)Cl.Cl.Cl.N1C=CC([CH:31]2[CH2:37][CH:36]3[NH:38][CH:33]([CH2:34][CH2:35]3)[CH2:32]2)=CC=1.C(=O)([O-])O.[Na+]>C(N(CC)CC)C.ClCCl>[N:1]1[CH:10]=[CH:5][CH:4]=[C:3]([CH:37]2[CH:36]3[N:38]([C:15]([N:1]4[C:10]5[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=5)[CH2:4][CH2:3][CH2:2]4)=[O:21])[CH:33]([CH2:34][CH2:35]3)[CH2:32][CH2:31]2)[CH:2]=1

Komponenten

7

Edukt 4

HCID 694601,2,3,4-TetrahydroquinolineHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 672677423-Pyridin-4-yl-8-azabicyclo[3.2.1]octane dihydrochloride

Produkt 1

HCID 249616021-[(4-Pyridin-3-yl-8-azabicyclo[3.2.1]oct-8-yl)carbonyl]-1,2,3,4-tetrahydroquinolineAusbeute 19,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel2×

Versuchsvorschrift

0.241 g of 1,2,3,4-tetrahydroquinoline, 20 ml of dichloromethane and 0.24 ml of triethylamine are placed in a 50 ml round-bottomed flask under a nitrogen atmosphere. 0.178 g of triphosgene is added at 0° C. and then the reaction mixture is left to stir at ambient temperature for 3 h. 0.34 g of 3-pyridin-4-yl-8-azabicyclo[3.2.1]octane dihydrochloride and 1.19 ml of triethylamine are subsequently added and the reaction mixture is then refluxed for three hours. 200 ml of a saturated aqueous solution of sodium hydrogen carbonate are added and the aqueous phase is then extracted three times with dichloromethane. The organic phases are combined, dried over sodium sulfate and evaporated under reduced pressure. The residue is chromatographed on silica gel with a 9/1 mixture of dichloromethane/methanol. 0.04 g of 1-[(4-pyridin-3-yl-8-azabicyclo[3.2.1]oct-8-yl)carbonyl]-1,2,3,4-tetrahydroquinoline is obtained.

Aufarbeitung

  1. waitthe reaction mixture is left
  2. temperaturethe reaction mixture is then refluxed for three hours
  3. extractionthe aqueous phase is then extracted three times with dichloromethane
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue is chromatographed on silica gel with a 9/1 mixture of dichloromethane/methanol

Quellen und Nachweise

ORD-Eintrag
ord-92cd74e0f83c4783921e5cd81f369fd9
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897773B2

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