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Water → Tert-butyl 4-[4-(3-cyanophenyl)-1,3-thiazol-2-yl]piperazine-1-carboxylate

HRID 2263279
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2263279
Br[C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[C:10]#[N:11])[N:6]=1.[N:15]1([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:10]([C:9]1[CH:8]=[C:7]([C:5]2[N:6]=[C:2]([N:18]3[CH2:17][CH2:16][N:15]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19]3)[S:3][CH:4]=2)[CH:14]=[CH:13][CH:12]=1)#[N:11]
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Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 687778083-(2-Bromo-1,3-thiazol-4-yl)benzonitrile

Produkt 1

HCID 68779422Tert-butyl 4-[4-(3-cyanophenyl)-1,3-thiazol-2-yl]piperazine-1-carboxylateAusbeute 50,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 3-(2-bromo-1,3-thiazol-4-yl)benzonitrile (990 mg, 4.90 mmol), tert-butyl piperazine-1-carboxylate (1.37 g, 7.34 mmol) and potassium carbonate (677 mg, 4.90 mmol) in dimethylformamide (16 ml) was stirred at 120° C. for 6 hours. Water was poured to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give 920 mg (50.7%) of the desired product as a solid.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-ffb06c7acbbc41fe8c8679592d98f6b7
Quelldatensatz
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07851473B2

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