Water → 4-(Dimethylamino)-2-phenylbutanenitrile

HRID 231593Notes

Reaction equation

HRID 231593 reaction equation
[C:1]1([CH2:7][C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:10][N:11]([CH3:15])[CH2:12][CH2:13]Cl.O>C1(C)C=CC=CC=1>[CH3:10][N:11]([CH3:15])[CH2:12][CH2:13][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]#[N:9]

Participants

5

Reactant 3

HCID 962WaterHCID 79012-Chloro-N,N-dimethylethylamineHCID 8794Phenylacetonitrile

Product 1

HCID 397394-(Dimethylamino)-2-phenylbutanenitrileYield 52.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

To a refluxing suspension of 35 g (0.90 mol) of NaNH2 in 750 ml of toluene was added, dropwise with mechanical stirring under N2, 100 g (0.85 mol) of phenylacetonitrile in 100 ml of toluene. The resulting suspension was stirred at reflux for a further 3 hr. Then, 92.5 g (0.86 mol) of 2-dimethylaminoethyl chloride in 50 ml of toluene was added dropwise, and the resulting dark suspension was first heated at reflux for 41/2 hr and then stirred at RT for 16 hr. Water (1.5 liters) was added to the mixture, and the organic layer was separated and extracted with 1N HCl. The acid extract was cooled in ice and then basified with 2.5N NaOH. The product was extracted from the basified solution with Et2O. The ethereal extract was dried (Na2SO4) and concentrated by evaporation. Distillation of the resulting crude oil afforded 35 g (52.5%) of the desired 4-dimethylamino-2-phenylbutanenitrile as a colorless oil; bp 95°-98°/0.1 mm.

Workup

  1. additionwas added
  2. stirringThe resulting suspension was stirred
  3. temperatureat reflux for a further 3 hr
  4. temperaturethe resulting dark suspension was first heated
  5. temperatureat reflux for 41/2 hr
  6. stirringstirred at RT for 16 hr
  7. customthe organic layer was separated
  8. extractionextracted with 1N HCl
  9. extractionThe acid extract
  10. temperaturewas cooled in ice
  11. extractionThe product was extracted from the basified solution with Et2O
  12. extractionThe ethereal extract
  13. dry with materialwas dried (Na2SO4)
  14. concentrationconcentrated by evaporation
  15. distillationDistillation of the resulting crude oil

Sources & evidence

ORD record
ord-588c7c13697e4f9081f22fbd52220588
Source dataset
uspto-grants-1989_07
Patent number
US04847301

Reaction notes

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