The hydrobromide of 9-hydroxyjulolidine was reacted with hydrochloride of 2-dimethylaminoethyl chloride, 2-(1-pyrrolidinyl)ethyl chloride, 2-(1-piperidinyl)ethyl chloride, and 3-dimethylaminopropyl chloride in ethanol in the presence of sodium ethoxide to give the title bases II-V which were transformed to dihydrochlorides. Heating of 1,2-epoxy-3-(1-naphthoxy)propane with 2,3,3-trimethyl-2-butylamine, 1-methylcyclopentylamine, 1-methylcyclohexylamine, 1-methylcycloheptylamine, and 10,11-dihydroxydibenzo[a,d]cycloheptene-5-amine in ethanol afforded the second part of the title compounds (VII-XI), prepared also in the form of hydrochlorides. Only the ethers II and V showed indications of possible antidepressant activity.
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Vejdělek et al. (1990) studied this question.