Water → 4-Diisopropylamino-2-phenyl-butyronitrile

HRID 262311Notes

Reaction equation

HRID 262311 reaction equation
[C:1]1([CH2:7][C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:11][CH2:12][N:13]([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15].[NH2-].[Na+].O>C1(C)C=CC=CC=1>[CH:14]([N:13]([CH:17]([CH3:19])[CH3:18])[CH2:12][CH2:11][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]#[N:9])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 73122-(Diisopropylamino)ethyl chlorideHCID 8794PhenylacetonitrileHCID 24533Sodium amide

Product 1

HCID 126122104-Diisopropylamino-2-phenyl-butyronitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of 58 parts of α-phenylacetonitrile in 300 parts by volume of toluene is added 83 parts of 2-chloro-N,N-diisopropylethylamine dissolved in 300 parts by volume of toluene. The mixture is heated with stirring to about 80° C. and then 22 parts of sodium amide is added slowly over a period of 30 minutes. The mixture is heated at 80° C. for another 30 minutes and then cooled to room temperature. 500 Parts by volume of water is then added to the mixture and the organic layer is separated and extracted with dilute hydrochloric acid. The aqueous acidic extract is made alkaline by the addition of dilute sodium hydroxide. The alkaline mixture is extracted with ether and the ether extract is dried over calcium sulfate, concentrated and distilled to afford α-[2-(diisopropylamino)ethyl]-α-phenylacetonitrile, as an oil boiling at about 120°-125° C. at 0.3 mm pressure. This compound is represented by the following structural formula ##STR12##

Workup

  1. temperatureThe mixture is heated
  2. temperatureThe mixture is heated at 80° C. for another 30 minutes
  3. temperaturecooled to room temperature
  4. customthe organic layer is separated
  5. extractionextracted with dilute hydrochloric acid
  6. extractionThe aqueous acidic extract
  7. additionby the addition of dilute sodium hydroxide
  8. extractionThe alkaline mixture is extracted with ether
  9. extractionthe ether extract
  10. dry with materialis dried over calcium sulfate
  11. concentrationconcentrated
  12. distillationdistilled

Sources & evidence

ORD record
ord-e5cd77413d4943df80c29879e405c1a6
Source dataset
uspto-grants-1979_05
Patent number
US04153797

Reaction notes

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