Dimethyl Sulfoxide → 1-[2-Chloro-5-(methyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperazine

HRID 419610

Reaktionsgleichung

Reaktionsgleichung von HRID 419610
[CH3:1][O:2][C:3]1[CH:8]=[C:7](F)[C:6]([Cl:10])=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].Cl.[CH3:15][S:16]([CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)(=[O:18])=[O:17].C([O-])([O-])=O.[K+].[K+].CS(C)=O>O>[Cl:10][C:6]1[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[C:3]([O:2][CH3:1])=[CH:8][C:7]=1[N:24]1[CH2:23][CH2:22][N:21]([CH2:20][CH2:19][S:16]([CH3:15])(=[O:17])=[O:18])[CH2:26][CH2:25]1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 534032891-Chloro-2-fluoro-4-methoxy-5-nitrobenzeneHCID 666496671-[2-(Methylsulfonyl)ethyl]piperazine hydrochloride

Produkt 1

HCID 594526341-[2-Chloro-5-(methyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperazineAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To 1-chloro-2-fluoro-4-(methyloxy)-5-nitrobenzene (Example 104, Step B) (0.822 g, 4.0 mmol), 4-[2-(methylsulfonyl)ethyl]piperazine hydrochloride (Example 148, Step B) (0.915 g, 4.0 mmol), and K2CO3 (1.7 g, 12 mmol) was added DMSO (8 mL). The reaction was heated to 100° C. for two days. The reaction was determined to be complete by TLC. The reaction mixture was diluted with H2O and extracted with DCM and EtOAc sequentially for two iterations. The organic was dried (MgSO4), filtered, and rotovapped down. Purification by flash chromatography provided the title compound of Step A (1.38 g, 91%). MS (M+H, ES+) 378.

Aufarbeitung

  1. extractionextracted with DCM and EtOAc sequentially for two iterations
  2. dry with materialThe organic was dried (MgSO4)
  3. filtrationfiltered
  4. customPurification by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-86d4005b11134c4792f37dc014c8d999
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093239B2

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