[NH2:1][CH:2]([CH2:14][CH3:15])[C:3]([NH:5][C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13])=O.C(OCC)(=O)C.O.[OH-].[Na+]>C(OCC)C>[CH3:12][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:13])[C:6]=1[NH:5][CH2:3][CH:2]([NH2:1])[CH2:14][CH3:15]2.5 g (66 mmoles) of lithium-aluminium-hydride are added in small portions, at room temperature, to a solution of 3.6 g (17.4 mmoles) of N-(2-aminobutyryl)-2,6-dimethyl-aniline in 40 ml of dry diethyl ether, and the resulting mixture is boiled for 3 hours. The mixture is cooled with ice, and 10 ml of ethyl acetate, 10 ml of water, finally 12 ml of a 5 n aqueous sodium hydroxide solution are added dropwise. The etheral phase is decanted, and the thick, gelly aqueous phase is washed thrice with 25 ml of diethyl ether, each. The etheral solutions are combined, washed thrice with 25 ml of water, each, dried over anhydrous magnesium sulfate, and the solvent is evaporated. The yellow, oily residue is distilled under reduced pressure to obtain 1.37 g of 1-(2,6-dimethylphenyl-amino)-2-amino-butane, b.p.: 122°-124° C./66.7 Pa, and 0.62 g of unreacted starting substance, b.p.: 158°-172° C./66.7 Pa. The product is obtained with a yield of 49%, calculated for the converted starting substance.
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