Water → N-Pyridin-3-yl-4-[3-(3-thienyl)phenyl]piperazine-1-carboxamide

HRID 1158721

Reaktionsgleichung

Reaktionsgleichung von HRID 1158721
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8](=[O:15])OCC(Cl)(Cl)Cl)[CH:2]=1.[S:16]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]=[C:23]([N:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[CH:24]=[CH:25][CH:26]=2)=[CH:17]1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]([N:30]2[CH2:31][CH2:32][N:27]([C:23]3[CH:24]=[CH:25][CH:26]=[C:21]([C:18]4[CH:19]=[CH:20][S:16][CH:17]=4)[CH:22]=3)[CH2:28][CH2:29]2)=[O:15])[CH:2]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 589851401-[3-(3-Thienyl)phenyl]piperazineHCID 68575380HCID 68575380, Verbindung

Produkt 1

HCID 16114127N-Pyridin-3-yl-4-[3-(3-thienyl)phenyl]piperazine-1-carboxamideAusbeute 37,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A mixed solution of 2,2,2-trichloroethyl pyridin-3-ylcarbamate (303 mg, 1.13 mmol), 1-[3-(3-thienyl)phenyl]piperazine (250 mg, 1.02 mmol) and diisopropylethylamine (0.356 ml, 2.05 mmol) in dimethylsulfoxide (3.5 ml) was stirred at 70° C. for 3 days. Water was poured into the reaction solution, and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduce pressure. The residue was purified by silica gel column chromatography (ethyl acetate), and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give the titled compound 139 mg (37.3%) as solid product.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  6. customrecrystallized from a mixed solvent of hexane and tetrahydrofuran

Quellen und Nachweise

ORD-Eintrag
ord-a0e2c83ccadb4bdf9c927cdbe862ecf0
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812025B2

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