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

HRID 2236678

反応式

HRID 2236678 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0c02f5d8e5b84e3980fef1c9ba841f10
出典データセット
uspto-grants-2010_05
特許番号
US07713994B2

関連ノート

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