Water → N-(3,4-Dimethylisoxazol-5-yl)-4-[3-(3-thienyl)phenyl]piperazine-1-carboxamide

HRID 1158720

Reaktionsgleichung

Reaktionsgleichung von HRID 1158720
ClC(Cl)(Cl)CO[C:5](=[O:14])[NH:6][C:7]1[O:11][N:10]=[C:9]([CH3:12])[C:8]=1[CH3:13].[S:17]1[CH:21]=[CH:20][C:19]([C:22]2[CH:23]=[C:24]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[CH:25]=[CH:26][CH:27]=2)=[CH:18]1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[CH3:12][C:9]1[C:8]([CH3:13])=[C:7]([NH:6][C:5]([N:31]2[CH2:32][CH2:33][N:28]([C:24]3[CH:25]=[CH:26][CH:27]=[C:22]([C:19]4[CH:20]=[CH:21][S:17][CH:18]=4)[CH:23]=3)[CH2:29][CH2:30]2)=[O:14])[O:11][N:10]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 589851401-[3-(3-Thienyl)phenyl]piperazineHCID 86245257HCID 86245257, Verbindung

Produkt 1

HCID 16113933N-(3,4-Dimethylisoxazol-5-yl)-4-[3-(3-thienyl)phenyl]piperazine-1-carboxamideAusbeute 19,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A mixed solution of 2,2,2-trichloroethyl(3,4-dimethylisoxazol-5-yl)carbamate (129 mg, 0.450 mmol), 1-[3-(3-thienyl)phenyl]piperazine (100 mg, 0.409 mmol) and diisopropylethylamine (0.143 ml, 0.818 mmol) in dimethylsulfoxide (1.5 ml) was stirred at 70° C. for 15 hours. 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 (hexane:ethyl acetate=3:7), and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give the titled compound 30.7 mg (19.6%) 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 (hexane:ethyl acetate=3:7)
  6. customrecrystallized from a mixed solvent of hexane and tetrahydrofuran

Quellen und Nachweise

ORD-Eintrag
ord-88c75a60a9314b91b8af8dc7309bc0e7
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812025B2

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