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

HRID 2262987
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2262987
Cl[C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:7]1([C:5]2[N:6]=[C:2]([N:23]3[CH2:22][CH2:21][N:20]([C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])[CH2:25][CH2:24]3)[S:3][CH:4]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27613592-Chloro-4-phenylthiazole

Produkt 1

HCID 68777857Tert-butyl 4-(4-phenyl-1,3-thiazol-2-yl)piperazine-1-carboxylateAusbeute 25,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

A solution of 2-chloro-4-phenyl-1,3-thiazole (1.54 mg, 7.87 mmol), 1-(tert-butoxycarbonyl)-piperazine (4.40 g, 23.6 mmol) and potassium carbonate (1.09 g, 7.87 mmol) in dimethylformamide (26 ml) was stirred at 120° C. for 2 hours. Water was poured to the reaction mixture, and the resulting solution 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 691 mg (25.4%) of tert-butyl 4-(4-phenyl-1,3-thiazol-2-yl)piperazine-1-carboxylate as a solid.

Aufarbeitung

  1. extractionthe resulting solution 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-951dbc3ab50141feb4c806e0575a73a6
Quelldatensatz
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07851473B2

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