Ammonium Chloride → 4-[6-(4-Isopropylpiperazin-1-yl)pyridazin-3-yl]benzonitrile

HRID 80928Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 80928
Cl[C:2]1[N:7]=[N:6][C:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl.[CH:17]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)([CH3:19])[CH3:18].[NH4+].[Cl-]>C(O)CCC>[CH:17]([N:20]1[CH2:25][CH2:24][N:23]([C:2]2[N:7]=[N:6][C:5]([C:8]3[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=3)=[CH:4][CH:3]=2)[CH2:22][CH2:21]1)([CH3:19])[CH3:18]

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 64052563-Chloro-6-(4-cyanophenyl)pyridazineHCID 161884471-Isopropyl-piperazine hydrochloride

Produkt 1

HCID 113587284-[6-(4-Isopropylpiperazin-1-yl)pyridazin-3-yl]benzonitrileAusbeute 70,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

To a solution of 4-(6-chloro-pyridazin-3-yl)-benzonitrile (20 g, 92.8 mmol) in 1-butanol (150 mL) was added 1-isopropyl-piperazine hydrochloride (29.8 g, 148.5 mmol) and NH4Cl (4.96 g, 92.8 mmol). The reaction mixture was heated at reflux for 48 h and then concentrated under reduced pressure. The residue was dissolved into a 10% solution of citric acid in water and filtered. Solid K2CO3 was added to the filtrate until pH 9. The precipitate was isolated and washed with water to give 4-[6-(4-isopropyl-piperazin-1-yl)-pyridazin-3-yl]-benzonitrile (20 g, 70%).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 48 h
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved into a 10% solution of citric acid in water
  5. filtrationfiltered
  6. additionSolid K2CO3 was added to the filtrate until pH 9
  7. customThe precipitate was isolated
  8. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-ef78ae68cc3948c1ad4153f13e37d26c
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846677B2

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