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1-Methylpiperazine → 5,6-Dihydro-2-(4-methyl-1-piperazinyl)-4H-imidazo[4,5,1-ij]quinoline

HRID 864640
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 864640
Cl[C:2]1[N:12]2[C:13]3[C:8]([CH2:9][CH2:10][CH2:11]2)=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=1.[CH3:14][N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>C(=O)(O)[O-].[Na+].O>[CH3:14][N:15]1[CH2:20][CH2:19][N:18]([C:2]2[N:12]3[C:13]4[C:8]([CH2:9][CH2:10][CH2:11]3)=[CH:7][CH:6]=[CH:5][C:4]=4[N:3]=2)[CH2:17][CH2:16]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 531671-MethylpiperazineHCID 152871052-Chloro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline

Produkt 1

HCID 153457165,6-Dihydro-2-(4-methyl-1-piperazinyl)-4H-imidazo[4,5,1-ij]quinolineAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A solution of 2-chloro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline (4.30 g) in 20 ml of N-methylpiperazine (18.06 g) was heated under reflux, under nitrogen, with stirring. After 30 mins, the solution was diluted with sodium bicarbonate solution (100 ml) and water (200 ml). The aqueous solution was extracted with chloroform. The organic phase was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by high performance liquid chromatography (silica gel; methanol). The appropriate fractions were collected and evaporated. The residue was crystallized from ether-petroleum ether to give 4.0 g (70%) of product, mp 112°-113° C.

Aufarbeitung

  1. temperatureunder reflux, under nitrogen
  2. extractionThe aqueous solution was extracted with chloroform
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by high performance liquid chromatography (silica gel; methanol)
  6. customThe appropriate fractions were collected
  7. customevaporated
  8. customThe residue was crystallized from ether-petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-b9cb644ecfc145e6b6813049ff1e8ee9
Quelldatensatz
uspto-grants-1996_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05563272

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