Alkylation of benzenesulfonamide, N-methylbenzenesulfonamide, acetanilide,N-n-butylacetamide, ε-caprolactam and phthalimide,with 3-dimethylaminopropylchloride hydrochloride in the presence of NaH or NaOH in DMSO yielded thefollowing amines: N-(3-dimethylaminopropyl)benzenesulfonamide, N-methyl-N-(3-dimethylaminopropyl)benzenesulfonamide, N-(3-dimethylaminopropyl)acetanilide,N-n-buty-N-(3-dimethylaminopropyl)acetamide, N-(3-dimethylaminopropyl)-ε-ca-prolactam, and N-(3-dimethylaminopropyl)phthalimide. The reaction times arrangedfrom 3 hours to 9 hours, and the yields 46% ~ 77%.Oxidation of N-(3-dimethylaminopropyl)benzenesulfonamide, N-methyl-N-(3-dimethylaminopropyl)benzenesulfonamide, N-(3-dimethylaminopropyl)acetanilide,N-n-buty-N-(3-dimethylaminopropyl)acetamide, N-(3-dimethylaminopropyl)-ε-capro-lactam and N-(3-dimethylaminopropyl)phthalimide with 28% aqueous hydrogenperoxide yielded the corresponding N-oxide compounds. The yields arranged from92% to 95%.The structure of the compounds were characterlized by IR, 1H NMR and 13C-NMR. The biological tests of these compounds is under way.
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