OC([C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])[CH2:16][CH2:15]2)C(N1CCNCC1)CC.BrC1C=CC(N[N+]([O-])=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>COC(C)CCO.[Cu]>[NH:18]1[C:19]2[C:14](=[CH:13][CH:12]=[CH:21][CH:20]=2)[CH2:15][CH2:16][C:17]1=[O:22]5.0 Grams of 6-(1-hydroxy-2-piperazinylbutyl)-3,4-dihydrocarbostyril, 3.5 g of p-bromonitroaniline, 1.8 g of potassium carbonate and 0.2 g of copper powder were mixed in 60 ml of 3-methoxybutanol and refluxed by heating for 5 hours. The reaction mixture was filtered and the mother liquid was concentrated by distillation under a reduced pressure to dryness. The residue thus obtained was extracted with methanol-chloroform and the solvent was removed by distillation to obtain a residue. The residue was purified and separated by a preparative silica-gel thin layer chromatograph to obtain 0.21 g of 6-{1-hydroxy-2-[4-nitrophenyl)-piperazinyl]butyl}-3,4-dihydrocarbostyril in yellow powdery crystals.
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