Sodium Iodide → HCID 22998315, Verbindung

HRID 1166427

Reaktionsgleichung

Reaktionsgleichung von HRID 1166427
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][CH2:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2.[CH3:20][O:21][C:22]([CH:24]1[CH:29]2[CH2:30][CH2:31][N:26]([CH2:27][CH2:28]2)[CH2:25]1)=[O:23].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(=O)CC.O.C1(C)C=CC=CC=1>[OH-:21].[CH:16]1[C:7]2[CH2:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:5]([CH2:4][CH2:3][CH2:2][N+:26]34[CH2:31][CH2:30][CH:29]([CH2:28][CH2:27]3)[CH:24]([C:22]([O:21][CH3:20])=[O:23])[CH2:25]4)[C:6]=2[CH:19]=[CH:18][CH:17]=1

Komponenten

8

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 2867795-(3-Chloropropyl)-10,11-dihydro-5H-dibenz[b,f]azepineHCID 2736953Methyl quinuclidine-3-carboxylate

Produkt 1

HCID 22998315HCID 22998315, VerbindungAusbeute 108,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

5-(3-Chloropropyl)-10,11-dihydro-5H-dibenzo[b,f]azepine (1.70 g, 6.25 mmol, prepared as described in example 1), and quinuclidine-3-carboxylic acid methyl ester (0.85 g, 5.0 mmol) were dissolved in 2-butanone (25 ml). Dry potassium carbonate (4.15 g, 30 mmol) and sodium iodide (0.75 g, 5 mmol) were added and the stirred mixture was heated at reflux temperature for 5 h. After cooling to room temperature, toluene (25 ml) and water (25 ml) were added. An oily precipitate was formed, which was separated from the solvents by decanting and dissolved in dichloromethane (30 ml). The solution was washed with water (2×30 ml), 1 N hydrochloric acid (2×30 ml), saturated sodium hydrogencarbonate solution (30 ml) and water (30 ml). The organic layer was dried over MgSO4. Evaporation in vacuo afforded 1.15 g 1-(3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)-1-propyl)-3-methoxycarbonyl-quinuclidinium hydroxide. The crude product was directly used in the next step without further purification.

Aufarbeitung

  1. temperaturethe stirred mixture was heated
  2. temperatureat reflux temperature for 5 h
  3. customAn oily precipitate was formed
  4. customwhich was separated from the solvents
  5. customby decanting
  6. dissolutiondissolved in dichloromethane (30 ml)
  7. washThe solution was washed with water (2×30 ml), 1 N hydrochloric acid (2×30 ml), saturated sodium hydrogencarbonate solution (30 ml) and water (30 ml)
  8. dry with materialThe organic layer was dried over MgSO4
  9. customEvaporation in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6e351571e2474690a9d8440974792de0
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06613791B1

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