[CH3:1][O:2][CH2:3][C:4]1([N:21]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:22](=[O:25])[CH2:23][CH3:24])[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)[CH2:6][CH2:5]1.[H][H]>[Ni].CO>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][CH2:10][N:7]2[CH2:6][CH2:5][C:4]([N:21]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:22](=[O:25])[CH2:23][CH3:24])([CH2:3][O:2][CH3:1])[CH2:9][CH2:8]2)=[CH:13][CH:14]=1A mixture of 14.8 parts of N-{4-(methoxymethyl)-1-[2-(4-nitrophenyl)ethyl]-4-piperidinyl}-N-phenylpropanamide and 200 parts of methanol is hydrogenated at normal pressure and at room temperature with 3 parts of Raney-nickel catalyst. After the calculated amount of hydrogen is taken up, the catalyst is filtered off and the filtrate is evaporated. The oily residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 5% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The oily residue is triturated in petroleumether. The product is filtered off and crystallized from a small amount of 2,2'-oxybispropane. It is filtered off and dried, yielding 8.23 parts of N-{1-[2-(4-aminophenyl)ethyl]-4-(methoxymethyl)-4-piperidinyl}-N-phenylpropanamide; mp. 106.2° C.
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