[CH:1](=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8].N.[H][H].[CH2:13]([NH2:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]=[CH2:20].[ClH:22]>[Ni].O.C(O)C>[ClH:22].[CH2:13]([NH2:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]=[CH2:20].[CH:1](=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8]A 100 ml autoclave with a magnetic stirrer was charged with 0.5 g of a Raney nickel catalyst (nickel content 53 weight %), 4 g of 7-octen-1-al, 20 g of ethanol, 4 g of water and 12 g of ammonia. Hydrogen was introduced into the autoclave at room temperature to 30 atmospheres. While maintaining the inside temperature at 35° C., the reaction was carried out with stirring. Approximately the theoretical amount of hydrogen was absorbed in 7 hours, when the reaction was stopped. The unreacted hydrogen and ammonia were released, and the liquid reaction mixture was analyzed by gas chromatography. It was revealed that the yield of 7-octenamine was 3.0 g (76% based on the charged 7-octen-1-al). As a byproduct, 0.4 g of the condensation product (Schiff base) of 7-octenamine with 7-octen-1-al was found and, when treated with diluted hydrochloric acid, yielded 7-octenamine hydrochloride and 7-octen-1-al; the 7 -octen-1-al forming the organic layer was separated and the aqueous layer was made basic with sodium hydroxide to give 0.2 g of 7-octenamine.
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