[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([NH:14][C:15](=O)[CH3:16])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[ClH:26]>CCOCC.CO.O.O1CCCC1>[ClH:26].[ClH:26].[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([NH:14][CH2:15][CH3:16])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1
A solution of 4 g. of trans N-[4-(p-aminophenyl)cyclohexyl]acetamide (prepared as in Example 83) in 150 ml. of tetrahydrofuran is added to 1.4 g. of lithium aluminum hydride in 10 ml. of tetrahydrofuran. The mixture is heated at reflux for about 3 hours and allowed to stand for about 16 hours. The cooled mixture is then heated with 1.4 ml. of water and 1.4 ml. of 15% aqueous sodium hydroxide solution and an additional 1.4 ml. of water. The solid is removed on a filter and the filtrate evaporated to dryness. The residual oily solid is suspended in ether. This mixture is filtered to give 0.63 g. of starting material melting at 190° to 194° C. The filtrate is evaporated to dryness and the residue dissolved in 75 ml. of tetrahydrofuran and added to 2 g. of lithium aluminum hydride in 200 ml. of tetrahydrofuran. After about 17 hours of heating at reflux temperature and about 17 hours at room temperature, the cooled mixture is heated with 2 ml. of water and 2 ml. of 15% aqueous sodium hydroxide solution and an additional 2 ml. of water. The solid is removed on a filter and the filtrate evaporated to dryness to give the crude product, which is dissolved in 50 ml. of methanol and then treated with 6.5 ml. of 4.7N hydrochloric acid in ether. The solution is evaporated to dryness and the residue recrystallized from methanol:ethyl acetate to give 3.55 g. (80% yield) of trans 4-(p-aminophenyl)-N-ethylcyclohexylamine dihydrochloride melting at 291° to 295° C.
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