Water → HCID 13587558, compound

HRID 544766Notes

Reaction equation

HRID 544766 reaction equation
[CH3:1][C:2]([C:21]#[N:22])([CH3:20])[CH2:3][C:4]1[C:9]([CH3:10])=[C:8]([CH3:11])[C:7]([CH2:12][C:13]([C:16]#[N:17])([CH3:15])[CH3:14])=[C:6]([CH3:18])[C:5]=1[CH3:19].[H-].C([Al+]CC(C)C)C(C)C.O>C1(C)C=CC=CC=1.CO>[CH3:14][C:13]([CH3:15])([CH2:16][NH2:17])[CH2:12][C:7]1[C:8]([CH3:11])=[C:9]([CH3:10])[C:4]([CH2:3][C:2]([CH3:1])([CH3:20])[CH2:21][NH2:22])=[C:5]([CH3:19])[C:6]=1[CH3:18]

Participants

6

Reactant 3

HCID 962Water2×HCID 135875681,4-Bis(2-methyl-2-cyanopropyl)tetramethylbenzeneHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 13587558HCID 13587558, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 1140TolueneSolvent2×

Procedure

In a 1-liter flask, equipped as described in Example 1(b), was put 6.17 g of 1,4-bis(2-methyl-2-cyanopropyl)tetramethylbenzene and 200 ml of reagent grade toluene which had been passed through acid alumina under nitrogen directly into the reaction vessel. With stirring at room temperature, 71.3 ml of a 24.1% solution of diisobutylaluminum hydride in toluene was added in 25 min. The mixture was refluxed for 22 hrs and allowed to stand at room temperature for 3 days. After the mixture had been cooled in an ice-water bath, a solution of 4 ml of water in 20 ml of methanol was added dropwise with stirring. This was followed by the dropwise addition of a solution of 20 ml of water in 40 ml of methanol. The mixture was then stirred at room temperature for several hours and allowed to stand at room temperature for 3 days. The mixture was filtered under nitrogen, the solid was washed thoroughly with toluene on the filter, and the combined filtrate and rinsings were distilled on the water pump. A solid residue resulted which, after further drying in a vacuum oven at room temperature, weighed 5.21 g and melted at 97° to 99°. Sublimation of this material at 125° to 145°/0.50 mm gave 1,4-bis(2,2-dimethyl-3-aminopropyl)tetramethylbenzene as a colorless crystalline solid melting at 97.5° to 98.5°.

Workup

  1. customIn a 1-liter flask, equipped
  2. temperatureThe mixture was refluxed for 22 hrs
  3. temperatureAfter the mixture had been cooled in an ice-water bath
  4. stirringwith stirring
  5. stirringThe mixture was then stirred at room temperature for several hours
  6. waitto stand at room temperature for 3 days
  7. filtrationThe mixture was filtered under nitrogen
  8. washthe solid was washed thoroughly with toluene on the filter
  9. distillationthe combined filtrate and rinsings were distilled on the water pump
  10. customA solid residue resulted which
  11. customafter further drying in a vacuum oven at room temperature

Sources & evidence

ORD record
ord-ec7391eabb994eb89c1cd97b9ef6e9f6
Source dataset
uspto-grants-1984_05
Patent number
US04451642

Reaction notes

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