Potassium Carbonate → 1-Isopropyl-4-(2-methyl-6-nitro-pyridin-3-yl)-piperazine

HRID 2264352Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2264352
Br[C:2]1[C:3]([CH3:11])=[N:4][C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=1.[CH:12]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)([CH3:14])[CH3:13].[C:21](=O)([O-])[O-:22].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CS(C)=O>[CH3:21][OH:22].[NH3:4].[CH:12]([N:15]1[CH2:20][CH2:19][N:18]([C:2]2[C:3]([CH3:11])=[N:4][C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=2)[CH2:17][CH2:16]1)([CH3:14])[CH3:13]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 780131-IsopropylpiperazineHCID 674264093-Bromo-2-methyl-6-nitropyridine

Produkt 2

HCID 21705897Ammonia methanolHCID 674271951-Isopropyl-4-(2-methyl-6-nitro-pyridin-3-yl)-piperazineAusbeute 172,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

Stir 3-bromo-2-methyl-6-nitro-pyridine (2.46 g), 1-isopropyl-piperazine (2.74 g), tetra-n-butyl ammonium iodide (418.69 mg) and potassium carbonate (1.72 g) in dimethyl sulfoxide (DMSO, 20 mL) at 65° C. overnight. Add EA and water, separate the phases and dry the organic layer over magnesium sulfate and remove the solvent under vacuum. Purify by strong cation exchange cartridge eluting with methanol and then methanol-NH3 2 N to afford 2.58 g of the title compound. MS (ES+): m/z=265 (M+H)+

Aufarbeitung

  1. customAdd EA and water, separate the phases
  2. dry with materialdry the organic layer over magnesium sulfate
  3. customremove the solvent under vacuum
  4. customPurify by strong cation exchange cartridge
  5. washeluting with methanol

Quellen und Nachweise

ORD-Eintrag
ord-bb929361ce1d4a23adef5f6d10274b36
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07855211B2

Notizen zur Reaktion

Wird geladen…