Diisopropylethylamine → 4-(6-Nitropyridin-3-yl)piperazin-2-one

HRID 592174Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 592174
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][C:12]1=[O:17].CCN(C(C)C)C(C)C>CS(C)=O>[N+:8]([C:5]1[N:6]=[CH:7][C:2]([N:14]2[CH2:15][CH2:16][NH:11][C:12](=[O:17])[CH2:13]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 231360Piperazin-2-oneHCID 8176205-Bromo-2-nitropyridine

Produkt 1

HCID 584479234-(6-Nitropyridin-3-yl)piperazin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a sealed tube were added 5-bromo-2-nitropyridine 141-1 (1.01 g, 5 mmol), piperazin-2-one 141-2 (0.6 g, 6 mmol), DIEA (1.8 mL, 18 mmol) and DMSO (6 mL). The reaction was heated to 120° C. and stirred for 16 hours. The reaction was cooled down to room temperature. DIEA was removed by rotary evaporation. The residue was triturated in 15 mL ethyl acetate. The solid was collected by filtration and washed with small amount of ethyl acetate to give 4-(6-nitropyridin-3-yl)piperazin-2-one 141-3 as light yellow solid. MS m/z 223.2 (M+1).

Aufarbeitung

  1. temperatureThe reaction was cooled down to room temperature
  2. customDIEA was removed by rotary evaporation
  3. customThe residue was triturated in 15 mL ethyl acetate
  4. filtrationThe solid was collected by filtration
  5. washwashed with small amount of ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-15f5106974294eb6823d1d79fdef3b48
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238646B2

Notizen zur Reaktion

Wird geladen…