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Dimethylformamide → 4-(3,5,6-Trichloropyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester

HRID 1804119
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1804119
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[C:4]([Cl:10])[N:3]=1.[C:11]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O.C1(C)C=CC=CC=1>[C:14]([O:13][C:11]([N:18]1[CH2:23][CH2:22][N:21]([C:2]2[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[C:4]([Cl:10])[N:3]=2)[CH2:20][CH2:19]1)=[O:12])([CH3:17])([CH3:15])[CH3:16]
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Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 169902,3,5,6-TetrachloropyridineHCID 143452tert-Butyl piperazine-1-carboxylate

Produkt 1

HCID 866587754-(3,5,6-Trichloropyridin-2-yl)piperazine-1-carboxylic acid tert-butyl esterAusbeute 85,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of 2,3,5,6-tetrachloropyridine (6.51 g), 1-Boc-piperazine (6.71 g) and potassium carbonate (9.95 g) were added dimethylformamide (15 mL) and toluene (30 mL), and the mixture was stirred at 100° C. for 2 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography (ethyl acetate:hexane) to give the title compound (9.42 g).

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by column chromatography (ethyl acetate:hexane)

Quellen und Nachweise

ORD-Eintrag
ord-49d385cb3fb24444b4d6d0ba4af67a9a
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08354401B2

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