Toluene → HCID 12612219, compound

HRID 262312Notes

Reaction equation

HRID 262312 reaction equation
[CH:1]([N:4]([CH:16]([CH3:18])[CH3:17])[CH2:5][CH2:6][CH:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:8]#[N:9])([CH3:3])[CH3:2].[NH2-].[Na+].C1(C)C=CC=CC=1.Cl[CH2:29][CH2:30][N:31]([CH:35]([CH3:37])[CH3:36])[CH:32]([CH3:34])[CH3:33]>O>[CH:16]([N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6][C:7]([CH2:29][CH2:30][N:31]([CH:35]([CH3:37])[CH3:36])[CH:32]([CH3:34])[CH3:33])([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:8]#[N:9])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 1140Toluene2×HCID 73122-(Diisopropylamino)ethyl chlorideHCID 24533Sodium amideHCID 126122104-Diisopropylamino-2-phenyl-butyronitrile

Product 1

HCID 12612219HCID 12612219, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 20 parts of α-[2-(diisopropylamino)ethyl]-α-phenylacetonitrile and 4 parts of sodium amide in 180 parts by volume of toluene is heated to about 100° C. over a period of 15 minutes and then 18 parts of 2-chloro-N,N-diisopropylethylamine in 70 parts by volume of toluene is added slowly over a period of 20 minutes. This mixture is heated at 105°-110° C. for an hour and then cooled to room temperature when 200 parts by volume of water is added. The organic layer is separated, dried over calcium sulfate, concentrated and distilled to afford α,α-bis[2-(diisopropylamino)ethyl]-α-phenylacetonitrile as an oil. This compound is identical with the compound of Example 2, Method A.

Workup

  1. temperatureThis mixture is heated at 105°-110° C. for an hour
  2. additionis added
  3. customThe organic layer is separated
  4. dry with materialdried over calcium sulfate
  5. concentrationconcentrated
  6. distillationdistilled

Sources & evidence

ORD record
ord-ff7fe36f6da6457a851792a7e2ffdfb8
Source dataset
uspto-grants-1979_05
Patent number
US04153797

Reaction notes

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