Hydrochloric Acid → 3-Chloro-5-(4-methyl-piperazin-1-yl)-benzonitrile

HRID 1639617Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1639617
F[C:2]1[CH:3]=[C:4]([Cl:10])[CH:5]=[C:6]([CH:9]=1)[C:7]#[N:8].C([O-])([O-])=O.[K+].[K+].[CH3:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.Cl>CS(C)=O.C(OCC)C>[Cl:10][C:4]1[CH:5]=[C:6]([CH:9]=[C:2]([N:21]2[CH2:22][CH2:23][N:18]([CH3:17])[CH2:19][CH2:20]2)[CH:3]=1)[C:7]#[N:8]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 27348413-Chloro-5-fluorobenzonitrile

Produkt 1

HCID 591389873-Chloro-5-(4-methyl-piperazin-1-yl)-benzonitrileAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

5-Fluoro-3-chloro-benzonitrile (1 g, 6.4 mmol) was dissolved in DMSO (20 ml) followed by addition of K2CO3 (1.3 g, 9.6 mmol) and 1-methyl piperazine (1.4 ml, 12.8 mmol). The reaction mixture was heated at 80° C. for 20 hours. Diethyl ether was added to the crude material (10 ml) then acidified with 1N HCl. A precipitate was filtered off from the crude reaction mixture to give 3-chloro-5-(4-methyl-piperazin-1-yl)-benzonitrile (1.4 g, 93% yield) as a white solid (LC/MS: Rt 1.83 [M+H]+ 236, acidic method).

Aufarbeitung

  1. filtrationA precipitate was filtered off from the crude
  2. customreaction mixture

Quellen und Nachweise

ORD-Eintrag
ord-05670eb37b624be7b575621aecd0d16c
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08110573B2

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