Process for the preparation of the pure Z isomer of 3-(4-bromophenyl)-N-methyl-3-(3-pyridyl)-allylamine

Process for the preparation of the pure Z isomer of 3-(4-bromophenyl)-N-methyl-3-(3-pyridyl)-allylamine

The pure Z isomer of 3-(4-bromophenyl)-N-methyl-3-(3-pyridyl)-allylamine of the formula (I) or one of its pharmaceutically acceptable acid addition salts is a highly selective inhibitor of the neuronal uptake of 5-hydroxytryptamine and can be used as antidepressants or neuroleptics. The said Z isome...

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Hauptverfasser: PER ARVID EMIL CARLSSON, BERNT SIGFRID EMANUEL CARNMALM, SVANTE BERTIL ROSS, CARL BENGT JOHAN ULFF
Format: Patent
Sprache:eng
Schlagworte:
CHEMISTRY
HETEROCYCLIC COMPOUNDS
HUMAN NECESSITIES
HYGIENE
MEDICAL OR VETERINARY SCIENCE
METALLURGY
ORGANIC CHEMISTRY
PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
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Zusammenfassung:The pure Z isomer of 3-(4-bromophenyl)-N-methyl-3-(3-pyridyl)-allylamine of the formula (I) or one of its pharmaceutically acceptable acid addition salts is a highly selective inhibitor of the neuronal uptake of 5-hydroxytryptamine and can be used as antidepressants or neuroleptics. The said Z isomer is prepared by hydrolysing a compound of the formula (VII) in which Z is an acyl group derived from a carboxylic acid or an organic sulphonyl group, to give a compound of the formula (I), and recrystallising the resulting mixture of stereoisomers, in the form of one of its acid addition salts, several times from a solvent in which the E and Z isomers display a considerably different solubility, and isolating the pure Z isomer. The compound of the formula (VII) is obtained by dehydration of the compound of the formula (VI):