The hydrobromide of 9-hydroxyjulolidine was reacted with hydrochloride of 2-dimethylaminoethyl chloride, 2-(I-pyrrolidinyl)ethyl chloride, 2-(I-piperidinyl)ethyl chloride, and 3-dimethylaminopropyl chloride in ethanol in the presence of sodium ethoxide to give the title bases 11-V which were transformed to dihydrochlorides. Heating of 1,2-epoxy-3-(I-naphthoxy)propane with 2,3, 3-trimethy 1-2-buty lamine, I-me thy Icyclopenty lamine, I-me thy Icyclohexy lamine, 1--methylcycloheptylamine, and 1O,II-dihydrodibenzo[a, d]cycloheptene-5-amine in ethanol afforded the second part of the title compounds (VII-Xl), prepared also in the form of hydrochi rides. Only the ethers 11 and V showed indications of possible antidepressant activity.
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