Diethylamine → 3-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-N,N-diethylpropionamide

HRID 1372396Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1372396
[CH3:1][C:2]1([CH3:17])[CH2:10][C:9]2[NH:8][CH:7]=[C:6]([CH2:11][CH2:12][C:13]([OH:15])=O)[C:5]=2[C:4](=[O:16])[CH2:3]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:30]([NH:32][CH2:33][CH3:34])[CH3:31]>ClCCl>[CH3:17][C:2]1([CH3:1])[CH2:10][C:9]2[NH:8][CH:7]=[C:6]([CH2:11][CH2:12][C:13]([N:32]([CH2:33][CH3:34])[CH2:30][CH3:31])=[O:15])[C:5]=2[C:4](=[O:16])[CH2:3]1

Komponenten

5

Edukt 3

HCID 8021DiethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 210718994,5,6,7-H4-6,6-Me2-4-oxo-indole-3-propanoic acid

Produkt 1

HCID 225710523-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-N,N-diethylpropionamideAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of 1.18 g of 3-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionic acid (5 mmol) in dichloromethane (25 mL) was added 0.97 g (6 mmol) of carbonyldiimidazole. After stirring at room temperature for 2 hours, 2.1 mL (20 mmol) of diethylamine was added. The mixture was stirred at room temperature overnight. The reaction was concentrated and the residue dissolved in dichloromethane, washed with brine, dried and concentrated to give 1.2 g (83% yield) of 3-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-N,N-diethyl-propionamide as a white solid. 1H-NMR (360 MHz, dimethylsulfoxide-d6) δ 10.91 (br s, 1H, NH), 6.46 (s, 1H), 3.20–3.29 (m, 4H, 2×CH2), 2.72–2.76 (m, 2H, CH2), 2.57 (s, 2H, CH2), 2.45 (m, 2H, CH2), 2.17 (s, 2H, CH2), 0.96–1.06 (m, 12H, 4×CH3). MS m/z 290 [M+].

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature overnight
  2. concentrationThe reaction was concentrated
  3. dissolutionthe residue dissolved in dichloromethane
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-793e3c418f9a4706bd9ef5e0e390f21c
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157577B2

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