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

HRID 2236678Notes

Reaction equation

HRID 2236678 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0c02f5d8e5b84e3980fef1c9ba841f10
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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