Acrylonitrile → 2-Benzyl-5-cyanoethyl-2,5-diazabicyclo[2.2.1]heptane

HRID 988957Notes

Reaction equation

HRID 988957 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[CH2:5]([N:12]1[CH2:17][CH:16]2[CH2:18][CH:13]1[CH2:14][NH:15]2)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1(C)C=CC=CC=1>[CH2:5]([N:12]1[CH2:17][CH:16]2[CH2:18][CH:13]1[CH2:14][N:15]2[CH2:3][CH2:2][C:1]#[N:4])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 5629322-Benzyl-2,5-diazabicyclo[2.2.1]heptane

Product 1

HCID 541916082-Benzyl-5-cyanoethyl-2,5-diazabicyclo[2.2.1]heptaneYield 89.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Freshly distilled acrylonitrile (2.5 g) is added to a solution of 3 g of 2-benzyl-2,5-diazabicyclo [2.2.1]heptane in 40 mL of anhydrous toluene and refluxed with vigorous stirring. The solution was cooled, filtered and evaporated. Bulb tube distillation (boiling point: 120°-130° C. at 0.01 mbar) resulted in 3.43 g of 142 as a colorless oil (88% of the theoretical yield).

Workup

  1. temperaturerefluxed with vigorous stirring
  2. temperatureThe solution was cooled
  3. filtrationfiltered
  4. customevaporated
  5. distillationBulb tube distillation (boiling point: 120°-130° C. at 0.01 mbar)

Sources & evidence

ORD record
ord-9ce6fa56805d4ab4915474ae422fc1cf
Source dataset
uspto-grants-2003_10
Patent number
US06638925B2

Reaction notes

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