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

HRID 55336

Reaktionsgleichung

Reaktionsgleichung von HRID 55336
C([C:4]1[CH:12]=[CH:11][C:10]2[NH:9][CH2:8][CH:7]3CC(N(CCC)CCC)C[C:5]=1[C:6]=23)(=O)C.C([N:25]([CH2:28]C)CC)C.ClC(OCC(Cl)(Cl)Cl)=[O:32]>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:32])[NH2:25]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 870632,2,2-Trichloroethyl chloroformateHCID 9839315(+)-6-Acetyl-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole

Produkt 1

HCID 7715242,3-dihydro-1H-indole-1-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (±)-6-acetyl-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole (2.3 g, 7.7 mmol) and triethylamine (1.1 ml, 8 mmol) in 90 ml CH2Cl2 under N2 was added dropwise a solution of 2,2,2-trichloroethyl chloroformate. The reaction mixture was stirred at room temperature for 1 hr. The CH2Cl2 solution was extracted with water and 1N HCl. The organic solution was washed with a saturated NaHCO3 solution and with a brine solution. The CH2Cl2 solution was dried (MgSO4) and concentrated in vacuo to give 3.3 g of the 1-carbamylindoline.

Aufarbeitung

  1. extractionThe CH2Cl2 solution was extracted with water and 1N HCl
  2. washThe organic solution was washed with a saturated NaHCO3 solution and with a brine solution
  3. dry with materialThe CH2Cl2 solution was dried (MgSO4)
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b483a291e9eb4a43811ec149ac543b50
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624944

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