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

HRID 2264352Notes

Reaction equation

HRID 2264352 reaction equation
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]

Participants

7

Reactant 3

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

Product 2

HCID 21705897Ammonia methanolHCID 674271951-Isopropyl-4-(2-methyl-6-nitro-pyridin-3-yl)-piperazineYield 172.2%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

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)+

Workup

  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

Sources & evidence

ORD record
ord-bb929361ce1d4a23adef5f6d10274b36
Source dataset
uspto-grants-2010_12
Patent number
US07855211B2

Reaction notes

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