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

HRID 2264352노트

반응식

HRID 2264352 반응식
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]

참가 물질

7

반응물 3

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

생성물 2

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

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 679Dimethyl Sulfoxide용매

실험 절차

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)+

후처리

  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

출처 및 근거

ORD 기록
ord-bb929361ce1d4a23adef5f6d10274b36
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07855211B2

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