3-Azabicyclo[3.2.2]nonane → 2-[2-(3-Azabicyclo[3.2.2]nonan-3-yl)ethyl]-1H-benz[de]-isoquinoline-1,3(2H)-dione

HRID 461435

Reaktionsgleichung

Reaktionsgleichung von HRID 461435
C12CCC(CC1)CNC2.C(N(C(C)C)CC)(C)C.Cl.[CH:20]12[CH2:28][CH2:27][CH:24]([CH2:25][CH2:26]1)[CH2:23][N:22]([CH2:29][CH2:30][N:31]1[C:40](=[O:41])[C:39]3[CH:42]=[CH:43][CH:44]=[C:37]4[C:38]=3[C:33](=[CH:34][CH:35]=[CH:36]4)[C:32]1=[O:45])[CH2:21]2>C1(C)C=CC=CC=1>[CH:24]12[CH2:27][CH2:28][CH:20]([CH2:26][CH2:25]1)[CH2:21][N:22]([CH2:29][CH2:30][N:31]1[C:40](=[O:41])[C:39]3[CH:42]=[CH:43][CH:44]=[C:37]4[C:38]=3[C:33](=[CH:34][CH:35]=[CH:36]4)[C:32]1=[O:45])[CH2:23]2

Komponenten

5

Edukt 3

HCID 92403-Azabicyclo[3.2.2]nonaneHCID 81531DiisopropylethylamineHCID 1317109692-[2-(3-azabicyclo[3.2.2]nonan-3-yl)ethyl]-1H-benz[de]isoquinoline-1,3(2H)-dione, hydrochloride

Produkt 1

HCID 213936912-[2-(3-Azabicyclo[3.2.2]nonan-3-yl)ethyl]-1H-benz[de]-isoquinoline-1,3(2H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

10 g. (0.025 mole) of the 4-methylbenzenesulfonate ester of example 1(b), 3.32 g. (0.027 mole) of 3-azabicyclo[3.2.2]nonane, and 3.27 g. (0.025 mole) of diisopropylethylamine are refluxed in 500 ml. of toluene for three hours. The reaction mixture is then cooled, washed with 10% KOH and water. The resulting toluene solution is shaken with 10% HCl and the resulting precipitate is filtered from the two phases. This salt is dissolved in a minimum of hot methanol, precipitated with ether, filtered, and dried at 80° under vacuum to yield 4.45 g. of 2-[2-(3-azabicyclo[3.2.2]nonan-3-yl)ethyl]-1H-benz[de]isoquinoline-1,3(2H)-dione, hydrochloride (1:1); m.p. 301°-302° (dec.).

Aufarbeitung

  1. temperatureThe reaction mixture is then cooled
  2. washwashed with 10% KOH and water
  3. filtrationthe resulting precipitate is filtered from the two phases
  4. dissolutionThis salt is dissolved in a minimum of hot methanol
  5. customprecipitated with ether
  6. filtrationfiltered
  7. customdried at 80° under vacuum
  8. customto yield 4.45 g

Quellen und Nachweise

ORD-Eintrag
ord-e8ef6f1e52ec4ed9bbc6ef0c16331df5
Quelldatensatz
uspto-grants-1977_12
Patentnummer
US04062953

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