Triethylamine → 3-[7,8,9,10-tetrahydro-6H-azepino[1,2-a]indol-11-yl]-3-(1-methyl-3-indolyl)furan-2,5-dione

HRID 863695Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 863695
[C:1](Cl)(=[O:5])[C:2](Cl)=O.[CH:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[C:10]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:11]12.[CH3:21][N:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([CH2:31][C:32]([OH:34])=[O:33])=[CH:23]1.C(N(CC)CC)C>ClCCl>[CH:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[C:9]([C:31]1([C:24]3[C:25]4[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=4)[N:22]([CH3:21])[CH:23]=3)[CH2:2][C:1](=[O:5])[O:34][C:32]1=[O:33])=[C:10]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:11]12

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 2541662-(1-methyl-1H-indol-3-yl)acetic acidHCID 111167347,8,9,10-tetrahydro-6H-azepino[1,2-a]indole

Produkt 1

HCID 196963163-[7,8,9,10-tetrahydro-6H-azepino[1,2-a]indol-11-yl]-3-(1-methyl-3-indolyl)furan-2,5-dioneAusbeute 22,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

1.5 g of oxalyl chloride were added dropwise to an ice-cold solution of 2.0 g of 7,8,9,10-tetrahydro-6H-azepino[1,2-a]indole (J. Org. Chem. 33, 1968, 4286) in 50 ml of dichloromethane. The mixture was stirred for 2 hours. The solvent was removed in a vacuum and the residue was dissolved in dichloromethane. The solution obtained was added to a solution of 2.2 g of 1-methyl-3-indolylacetic acid and 2.73 g of triethylamine in 50 ml of dichloromethane. The mixture was stirred and then concentrated. The residue was chromatographed on silica gel with dichloromethane and there was obtained 1.0 g of 3-[7,8,9,10-tetrahydro-6H-azepino[1,2-a]indol-11-yl]-3-(1-methyl-3-indolyl)furan-2,5-dione of melting point 257°-259° C.

Aufarbeitung

  1. customThe solvent was removed in a vacuum
  2. dissolutionthe residue was dissolved in dichloromethane
  3. customThe solution obtained
  4. stirringThe mixture was stirred
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-b40e585f1f6b4f499d8db2815a94f907
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05721245

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