O[CH:2]1[CH2:11][CH2:10][CH:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:3]1.[OH-].[Ca+2].[OH-].[NH3:15].[H][H]>C([O-])=O.[Cu+2].C([O-])=O>[CH:3]1([NH:15][CH:8]2[CH:9]3[CH:4]([CH2:3][CH2:2][CH2:11][CH2:10]3)[CH2:5][CH2:6][CH2:7]2)[CH:4]2[CH:9]([CH2:8][CH2:7][CH2:6][CH2:5]2)[CH2:10][CH2:11][CH2:2]1150 kg of 2-hydroxydecahydronaphthalene, 3 kg of copper formate and 2 kg of calcium hydroxide were gassed at 190° C. with excess ammonia and hydrogen (volume ratio of 8:1) for 4 hours. The supply of ammonia was then discontinued and the mixture was gassed with just hydrogen at the reaction temperature for a further 2 hours. Working up was carried out in the conventional manner. Bis(decahydronaphthyl)amine was obtained in a yield of 98% of theory.
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