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Dimethylformamide → 1-(3-Dimethylaminobutyl)-3-(3-diethylaminopropylamino)indazole

HRID 484904
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 484904
CN(C)C=O.[CH3:6][N:7]([CH3:22])[CH:8]([CH3:21])[CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([NH2:20])=[N:12]1.Br.Br[CH2:25][CH2:26][CH2:27][N:28]([CH2:31][CH3:32])[CH2:29][CH3:30].C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl.O>[CH3:22][N:7]([CH3:6])[CH:8]([CH3:21])[CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([NH:20][CH2:25][CH2:26][CH2:27][N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[N:12]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 12639158(3-Bromopropyl)diethylamine hydrobromideHCID 132105851-(3-Dimethylaminobutyl)-3-aminoindazole

Produkt 1

HCID 30308381-(3-Dimethylaminobutyl)-3-(3-diethylaminopropylamino)indazoleAusbeute 55,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To 60 ml of anhydrous N, N-dimethylformamide were added 7.50 g of the 1-(3-dimethylaminobutyl)-3-aminoindazole, 8.98 g of 3-bromopropyldiethylamine hydrobromide and 7.89 g of anhydrous potassium carbonate, and the mixture was stirred for 12 hours at 80° C. After cooling, the mixture was added with 80 ml of water and extracted with diethyl ether. The diethyl ether layer was extracted three times with 2N hydrochloric acid, and the hydrochloric acid layer was washed with diethyl ether. The pH of the layer was adjusted to at least 11 with potassium carbonate, and the alkali layer was extracted three times with chloroform. The chloroform layer was dried over anhydrous sodium sulfate, and chloroform was removed under reduced pressure. The residue thus obtained was subjected to an alumina-column chromatography (alumina: 200 g) using chloroform as the developing solvent to give 6.18 g of 1-(3-dimethylaminobutyl)-3-(3-diethylaminopropylamino)indazole having the following analytical values in a yield of 52%.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionextracted with diethyl ether
  3. extractionThe diethyl ether layer was extracted three times with 2N hydrochloric acid
  4. washthe hydrochloric acid layer was washed with diethyl ether
  5. extractionthe alkali layer was extracted three times with chloroform
  6. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate, and chloroform
  7. customwas removed under reduced pressure
  8. customThe residue thus obtained

Quellen und Nachweise

ORD-Eintrag
ord-c38028d613294fb585769c37af64ce6d
Quelldatensatz
uspto-grants-1985_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04533731

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