p-Fluoronitrobenzene → 2-Methyl-5-(4-nitro-phenyl)-2,5-diaza-bicyclo[2.2.1]heptane

HRID 2236678

반응식

HRID 2236678 반응식
[CH3:1][N:2]1[CH2:7][CH:6]2[CH2:8][CH:3]1[CH2:4][NH:5]2.F[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[CH3:1][N:2]1[CH2:7][CH:6]2[CH2:8][CH:3]1[CH2:4][N:5]2[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1

참가 물질

5

반응물 3

HCID 9590p-FluoronitrobenzeneHCID 81531DiisopropylethylamineHCID 102194032-Methyl-2,5-diazabicyclo[2.2.1]heptane

생성물 1

HCID 189990942-Methyl-5-(4-nitro-phenyl)-2,5-diaza-bicyclo[2.2.1]heptane수율 65.9%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of 2-methyl-2,5-diaza-bicyclo[2.2.1]heptane (0.4402 g, 1.6 mmol), p-fluoro-nitrobenzene (0.56 mL, 5.4 mmol), N,N-diisopropylethylamine (0.84 mL, 4.82 mmol) in 5 mL of acetonitrile is heated at 100° C. overnight. After the solvent is removed, the residue is treated with saturated sodium bicarbonate solution and extracted with chloroform. The organic layer is washed with brine, dried over magnesium sulfate, filtered, and evaporated to dryness. The oil is washed with hexane to give a yellow solid, which is recrystallized from ethyl acetate/hexane to yield 0.246 g (65% yield) of 2-methyl-5-(4-nitro-phenyl)-2,5-diaza-bicyclo[2.2.1]heptane.

후처리

  1. customAfter the solvent is removed
  2. additionthe residue is treated with saturated sodium bicarbonate solution
  3. extractionextracted with chloroform
  4. washThe organic layer is washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. washThe oil is washed with hexane
  9. customto give a yellow solid, which
  10. customis recrystallized from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-0c02f5d8e5b84e3980fef1c9ba841f10
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07713994B2

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