Sodium Hydroxide → 3-(3-dimethylaminopropyl)-4,5,6,7-tetrahydro-1H-indole

HRID 1836121

Reaktionsgleichung

Reaktionsgleichung von HRID 1836121
[CH3:1][N:2]([CH3:17])[C:3](=O)[CH2:4][CH2:5][C:6]1[C:14]2[C:13](=O)[CH2:12][CH2:11][CH2:10][C:9]=2[NH:8][CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.O>[CH3:17][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][C:6]1[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[NH:8][CH:7]=1

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 22571143HCID 22571143, Verbindung

Produkt 1

HCID 111484413-(3-dimethylaminopropyl)-4,5,6,7-tetrahydro-1H-indoleAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N,N-Dimethyl-3-(4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionamide (8 g, 0.034 mol) was suspended in 125 ml of tetrahydrofuran and lithium aluminum hydride (5.2 g, 0.136 mol) was slowly added. The mixture was refluxed over night, cooled in ice, and 5 ml of water and then 5 ml of 15% sodium hydroxide solution was slowly added. The mixture was stirred for 45 minutes. Water (15 ml) and sodium sulfate were added and the mixture filtered to remove solids. The solids were washed with ethyl acetate and the filtrate was concentrated to give dimethyl-[3-(4,5,6,7-tetrahydro-1H-indol-3-yl)-propyl]-amine (6.3 g, 90% yield).

Aufarbeitung

  1. temperatureThe mixture was refluxed over night
  2. temperaturecooled in ice
  3. filtrationthe mixture filtered
  4. customto remove solids
  5. washThe solids were washed with ethyl acetate
  6. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-57587fae93fd4b91a63c9f8689843fe9
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06777417B2

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