1-Isopropylpiperazine → 1-Isopropyl-4-(6-nitropyridin-3-yl)piperazine

HRID 449608Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 449608
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[CH:11]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)([CH3:13])[CH3:12]>CS(C)=O.O>[CH:11]([N:14]1[CH2:19][CH2:18][N:17]([C:2]2[CH:7]=[N:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:16][CH2:15]1)([CH3:13])[CH3:12]

Komponenten

5

Edukt 2

HCID 780131-IsopropylpiperazineHCID 8176205-Bromo-2-nitropyridine

Produkt 1

HCID 575020971-Isopropyl-4-(6-nitropyridin-3-yl)piperazineAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To 5-bromo-2-nitropyridine (1.0 g, 4.93 mmol, Eq: 1.00) in DMSO (10.0 ml) was added 1-isopropylpiperazine (632 mg, 4.93 mmol, Eq: 1.00), and the resulting solution was heated at 70° C. for 18 hours. The solution was cooled to room temperature. The solution was diluted with 50 ml water. The resulting solid was filtered. The solid was washed with water and dried under vacuum. The crude material was purified by flash chromatography (silica gel, 80 g, 0% to 3% MeOH/DCM gradient) to give 1-isopropyl-4-(6-nitropyridin-3-yl)piperazine (788 mg, 64%). LC/MS-ESI observed [M+H]+ 251.

Aufarbeitung

  1. temperatureThe solution was cooled to room temperature
  2. filtrationThe resulting solid was filtered
  3. washThe solid was washed with water
  4. customdried under vacuum
  5. customThe crude material was purified by flash chromatography (silica gel, 80 g, 0% to 3% MeOH/DCM gradient)

Quellen und Nachweise

ORD-Eintrag
ord-d84d17cbcbd2469093a892031e15f024
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481540B2

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