alpha,alpha,alpha',alpha'-Tetramethyl-1,3-benzenedipropionitrile → 1,3-Bis(2,2-dimethyl-3-aminopropyl)benzene

HRID 66176Notes

Reaction equation

HRID 66176 reaction equation
[CH3:1][C:2]([C:17]#[N:18])([CH3:16])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][C:11]([C:14]#[N:15])([CH3:13])[CH3:12])[CH:5]=1.[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[CH3:12][C:11]([CH3:13])([CH2:14][NH2:15])[CH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH2:3][C:2]([CH3:1])([CH3:16])[CH2:17][NH2:18])[CH:5]=1

Participants

4

Reactant 2

HCID 13587560alpha,alpha,alpha',alpha'-Tetramethyl-1,3-benzenedipropionitrileHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 135875571,3-Bis(2,2-dimethyl-3-aminopropyl)benzeneYield 45.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

In a 1-liter flask, equipped with a paddle stirrer, a reflux condenser, capped with a nitrogen bubbler, and an addition funnel, was placed 7.50 g of 1,3-bis(2-methyl-2-cyanopropyl)benzene and 250 ml of reagent grade toluene which had been passed through acid alumina under nitrogen directly into the reaction vessel. With stirring at room temperature, 107 ml of a 25% solution of diisobutylaluminum hydride in toluene was added in 1 hr. The mixture was refluxed for 17 hrs 15 min. The mixture was then worked up as described in Example 9(a). Upon distillation of the isolated product through a small Vigreux still, there was obtained 3.51 g of 1,3-bis(2,2-dimethyl-3-aminopropyl)benzene as a colorless liquid distilling at 105°-110°/0.05 mm.

Workup

  1. customIn a 1-liter flask, equipped with a paddle stirrer, a reflux condenser
  2. customcapped with a nitrogen bubbler, and an addition funnel
  3. temperatureThe mixture was refluxed for 17 hrs 15 min
  4. distillationUpon distillation of the isolated product through a small Vigreux still

Sources & evidence

ORD record
ord-09a1eae97c4d4c6da1a01401bb493778
Source dataset
uspto-grants-1978_12
Patent number
US04130579

Reaction notes

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