Triethylamine → 2,3-dihydro-1H-indole-1-carboxamide

HRID 233781

Reaktionsgleichung

Reaktionsgleichung von HRID 233781
C([C:4]1[CH:12]=[CH:11][C:10]2[NH:9][CH2:8][C@H:7]3C[C@@H](N(CCC)CCC)C[C:5]=1[C:6]=23)(=O)C.C([N:25]([CH2:28]C)CC)C.ClC(Cl)(Cl)C[O:33]C(Cl)=O>C(Cl)Cl>[C:28]([N:9]1[C:10]2[C:6](=[CH:5][CH:4]=[CH:12][CH:11]=2)[CH2:7][CH2:8]1)(=[O:33])[NH2:25]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 870632,2,2-Trichloroethyl chloroformateHCID 18652841(+) (2aS,4R)-6-acetyl-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indol

Produkt 1

HCID 7715242,3-dihydro-1H-indole-1-carboxamideAusbeute 270,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of (+)(2aS,4R)-6-acetyl-4-(di-n-propylamino) -1,2,2a,3,4,5-hexahydrobenz[cd]indole (1.7 g, 5.7 mmol) and triethylamine (0.8 ml, 6 mmol) in 90 ml CH2Cl2 was added dropwise a solution of 2,2,2-trichloroethylchloroformate (1.3 g, 6 mmol) in 10 ml CH2Cl2. The reaction mixture was stirred at room temperature for one hour and then extracted with water and 1N HCl. The organic solution was washed with a saturated NaHCO3 solution, a saturated brine solution, dried over MgSO4 and then concentrated to dryness in vacuo to give 2.5 g of the 1-carbamylindoline.

Aufarbeitung

  1. extractionextracted with water and 1N HCl
  2. washThe organic solution was washed with a saturated NaHCO3 solution
  3. dry with materiala saturated brine solution, dried over MgSO4
  4. concentrationconcentrated to dryness in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-55f50d4acfb9433a9468023d4c5063f9
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05594019

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