[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]In a 1-liter flask, equipped as described in Example 9(a), 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°-99°. Sublimation of this material at 125°-145°/0.50 mm gave 1,4-bis(2,2-dimethyl-3-aminopropyl)tetramethylbenzene as a colorless crystalline solid melting at 97.5°-98.5°.
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