Potassium Carbonate → 2-(4-Isopropylpiperazin-1-yl)-5-nitrobenzonitrile

HRID 633449Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 633449
F[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].[CH:13]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)([CH3:15])[CH3:14].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH:13]([N:16]1[CH2:21][CH2:20][N:19]([C:2]2[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=2[C:4]#[N:5])[CH2:18][CH2:17]1)([CH3:15])[CH3:14]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 780131-IsopropylpiperazineHCID 5194172-Fluoro-5-nitrobenzonitrile

Produkt 1

HCID 339954542-(4-Isopropylpiperazin-1-yl)-5-nitrobenzonitrileAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2-fluoro-5-nitrobenzonitrile (1.08 g, 6.50 mmol, 1 equiv), 1-isopropylpiperazine (1.0 g, 7.80 mmol, 1.2 equiv), and K2CO3 (2.69 g, 19.50 mmol, 3 equiv) in DMF (20 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between excess water and EtOAc, and then the layers were separated. The aqueous layer was extracted with EtOAc 2×, and the combined organic layer was washed with brine 1×. The organic layer was dried over Na2SO4, filtered, and concentrated to dryness to provide 2-(4-isopropylpiperazin-1-yl)-5-nitrobenzonitrile (1.76 g, 99% yield) as a brown oil that was used without further purification.

Aufarbeitung

  1. customThe reaction mixture was partitioned between excess water and EtOAc
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with EtOAc 2×
  4. washthe combined organic layer was washed with brine 1×
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-30c52d4c6ec54ae1af697a1ae8c3f31f
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321763B2

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