4-Aminoaliphatic-2,3,5,6-[dibenzobicyclo[5.1.0]octanes] and salt

Details 4-Aminoaliphatic-2,3,5,6-[dibenzobicyclo[5.1.0]octanes] and salt 4-Aminoaliphatic-2,3,5,6-[dibenzobicyclo[5.1.0]octanes] and salt

1972-11-28

1981-03-24

Hines, Robert V.

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

2605011, 26050118, 424316, 424330, 564380, C07C 8728

Patent

active

042582113

ABSTRACT:
This invention concerns 2,3,5,6-dibenzobicyclo[5.1.0]octanes which may be substituted at the 4-position by either halogen, ketonic oxygen or hydroxyl. These compounds are prepared from 5H-dibenzo[a,d]cyclohepten-5-one by reaction with ethyl trichloroacetate in the presence of sodium methoxide to give 8,8-dichloro-2,3,5,6-dibenzobicyclo[5.1.0]octan-4-one which is reduced to the corresponding 4-hydroxy compound. The resulting 4-hydroxy compound is dehalogenated and converted to the corresponding 4-chloro or 4-keto compound. The 4-substituted compounds are useful in preparing other compounds of our invention.
4-Dialkylaminopropylidenedibenzobicyclo[5.1.0]octane compounds and 4-dialkylaminopropyldibenzobicyclo[5.1.0]octane compounds, useful as antidepressant agents, are prepared from, respectively, dibenzobicyclo[5.1.0]octan-4-one by reaction with a dialkylaminopropyl Grignard reagent followed by dehydration of the resulting carbinol or by reaction of a 4-halo-2,3,5,6-dibenzobicyclo[5.1.0]octane with a dialkylaminopropyl Grignard reagent. Both the dialkylaminopropyl and the dialkylaminopropylidene compounds are converted to the corresponding monoalkylamino compounds by dealkylation.

REFERENCES:
patent: 3547933 (1970-12-01), Coyne et al.
patent: 3574199 (1971-04-01), Coyne et al.

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