Water → 3-Methyl-4-(piperazin-1-yl)benzonitrile

HRID 874534Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 874534
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:10].[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.O>CS(C)=O>[CH3:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)[C:6]#[N:7]

Komponenten

5

Edukt 3

HCID 962WaterHCID 4837PiperazineHCID 27791804-Fluoro-3-methylbenzonitrile

Produkt 1

HCID 600511423-Methyl-4-(piperazin-1-yl)benzonitrileAusbeute 69,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a solution of 4-fluoro-3-methylbenzonitrile (2.5 g, 18.50 mmol) in DMSO (Volume: 10.0 mL) was added piperazine (7.97 g, 92 mmol) at 23° C. The reaction was stirred at 140° C. for 16 hr. The reaction mixture was poured into H2O (100 mL) and the reaction vessel was rinsed with H2O (50 mL). The resulting suspension was filtered, rinsed with H2O (3×10 mL) and the resulting solid was dried in vacuo to provide 3-methyl-4-(piperazin-1-yl)benzonitrile (2.593 g, 12.88 mmol, 69.6% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.21-2.30 (m, 3 H) 2.57-2.70 (m, 1 H) 2.83 (s, 8 H) 7.03-7.09 (m, 1 H) 7.55-7.62 (m, 2 H). ESI-MS: m/z 202.1 (M+H)1. mp=214.1-231.2° C.

Aufarbeitung

  1. washthe reaction vessel was rinsed with H2O (50 mL)
  2. filtrationThe resulting suspension was filtered
  3. washrinsed with H2O (3×10 mL)
  4. customthe resulting solid was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1a3d34a62a774ba4b8e46c2c122399db
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08980902B2

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