Morpholine → 4-(6-Nitropyridin-3-yl)morpholine

HRID 586517

반응식

HRID 586517 반응식
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][O:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CS(C)=O.C(OCC)(=O)C>[N+:8]([C:5]1[N:6]=[CH:7][C:2]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

참가 물질

7

반응물 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 8176205-Bromo-2-nitropyridine

생성물 1

HCID 29279734-(6-Nitropyridin-3-yl)morpholine수율 54.8%

시약·촉매·용매 3

HCID 67553Tetrabutylammonium Iodide촉매HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

5-Bromo-2-nitropyridine (5.14 g, 25.3 mmol), tetra-n-butyl ammonium iodide (0.467 g, 1.27 mmol), morpholine (2.43 g, 27.9 mmol) and potassium carbonate (3.85 g, 27.9 mmol) were mixed in DMSO (50 mL). The reaction mixture was warmed to 80° C. for 15 hours. The reaction mixture was diluted with ethyl acetate and the solids removed by filtration. The organic filtrate was washed with water, then the solvent evaporated. The residue was then triturated with a dichloromethane/hexanes mixture to provide 4-(6-nitro-pyridin-3-yl)-morpholine as brown needles (2.90 g, 54.8%). 1H NMR δ (400 MHz, CDCl3) 8.16 (m, 1H), 7.97 (d, J=2.9 Hz, 1H), 7.15 (dd, J=3.2, 9.3 Hz, 1H), 3.45 (m, 4H), 1.72 (m, 4H).

후처리

  1. customthe solids removed by filtration
  2. washThe organic filtrate was washed with water
  3. customthe solvent evaporated
  4. customThe residue was then triturated with a dichloromethane/hexanes mixture

출처 및 근거

ORD 기록
ord-37fe36c73def478fa5119c4c399ed3e8
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06936612B2

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