Water → Tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate

HRID 494021

Reaktionsgleichung

Reaktionsgleichung von HRID 494021
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][N:5]=1)([O-:3])=[O:2].[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+].O>CN(C)C=O>[N+:1]([C:4]1[N:5]=[CH:6][C:7]([N:21]2[CH2:20][CH2:19][N:18]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:23][CH2:22]2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 8176205-Bromo-2-nitropyridine

Produkt 1

HCID 11243758Tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylateAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A solution is prepared of 1 g (4.9 mM) of 2-nitro-5-bromopyridine and 917 mg (4.9 mM) of N-Boc-piperazine in 10 ml of dimethylformamide and 1.02 g (7.4 mM) of potassium carbonate are added. The reaction mixture is agitated at 120° C. for 36 hours and then cooled. 50 ml of water are then added and extraction is carried out with ethyl acetate. The organic phase obtained is washed with water, dried and concentrated under reduced pressure. The crude product is purified by silica gel chromatography in eluting with the aid of a toluene/isopropanol mixture (98/2; v/v). The product sought after is thus obtained as a yellow solid (yield=33%).

Aufarbeitung

  1. additionare added
  2. temperaturecooled
  3. extractionextraction
  4. customThe organic phase obtained
  5. washis washed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product is purified by silica gel chromatography
  9. washin eluting with the aid of a toluene/isopropanol mixture (98/2; v/v)

Quellen und Nachweise

ORD-Eintrag
ord-be504eb9429b40eaa9d3ea8ff4b4dd3b
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538111B2

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