In:
Collection of Czechoslovak Chemical Communications, Institute of Organic Chemistry & Biochemistry, Vol. 49, No. 11 ( 1984), p. 2520-2530
Kurzfassung:
Reactions of 2-chloro- and 2-methyl-6,11-dihydrodibenzo[ b,e ]thiepin-11-ol with 2-bromoethanol in the presence of sulfuric acid in boiling benzene afforded the 2-bromoethyl ethers VIa and VIb which were transformed by substitution reactions with 1-methylpiperazine, 1-(2-hydroxyethyl)-piperazine and 1-(ethoxycarbonyl)piperazine to the title compounds. Alkaline hydrolysis of the carbamate IVa gave the secondary amine IIIa . Treatment of the bromo ether VIa with 4-(4-chloro-3-trifluoromethylphenyl)piperidin-4-ol resulted in the piperidine derivative VIIa . Substitution reaction of 11-chloro-6,11-dihydrodibenzo[ b,e ]thiepin with 1-(2-methoxyethyl)piperazine and 1-(2-ethoxyethyl)piperazine led to the amino ethers VIII and IX . Reaction of 11-chloro-11-phenyl-6,11-dihydrodibenzo[ b,e ]thiepin with 2-dimethylaminoethanethiol in dimethylformamide at 90°C gave a mixture of two isomeric bases which was separated to the expected sulfide X and the base XII , resulting evidently after the rearrangement of the primary carbocation. A similar reaction of 3-dimethylaminopropanethiol afforded a single product of structure XI . Out of the compounds prepared, the ether VIII was found most interesting: it is little toxic and has significant antireserpine activity in two tests (is considered a potential antidepressant). The ethers Iab, Iab, IIIa and VIIa did not reveal the expected neuroleptic activity.
Materialart:
Online-Ressource
ISSN:
0010-0765
,
1212-6950
DOI:
10.1135/cccc19842520
Sprache:
Englisch
Verlag:
Institute of Organic Chemistry & Biochemistry
Publikationsdatum:
1984
