Collect. Czech. Chem. Commun. 1987, 52, 2564-2571

Potential antidepressants: 3-Methyl-6-dimethylamino-1,2-diphenylhexan-3-ol and related compounds

Irena Červená, Jiří Holubek, Emil Svátek, Martin Valchář and Miroslav Protiva

Research Institute for Pharmacy and Biochemistry, 130 60 Prague 3


3,4-Diphenylbutan-2-one (III) and 3-methyl-3-phenylbutan-2-one were transformed by treatment with 3-dimethylaminopropylmagnesium chloride and 1-methyl-4-piperidylmagnesium chloride to the amino alcohols VI, VII, and X. Compound VI was dehydrated to the olefinic amine VIII, and reduced to the saturated amine IX. 2-(3-Fluoro-4-hydroxyphenyl)ethylamine (XI) was prepared by a modified route via the methoxy precursor XV. Only the amino alcohol VI showed antireserpine activity in one test. The fluoro analogue of dopamine XI did show neither the dopaminomimetic nor the antidopaminergic character.