Collect. Czech. Chem. Commun. 1990, 55, 1290-1296

Potential antidepressants and tranquillizers: Synthesis of some 9-(aminoalkoxy)-2,3,6,7-tetrahydro-1H,5H-benzo[ij] quinolizines and 1-(substituted amino)-3-(1-naphthoxy)-2-propanols

Zdeněk Vejdělek and Miroslav Protiva

Research Institute for Pharmacy and Biochemistry, 130 60 Prague 3


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.