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.
这项发明涉及2,3,5,6-二苯并[5.1.0]
辛烷,可以在4位被卤素、酮氧或羟基取代。这些化合物是从
5H-二苯并[a,d]环庚烯-5-酮与
三氯乙酸乙酯在甲氧基
钠存在下反应制备而成,得到8,8-二
氯-2,3,5,6-二苯并[5.1.0]
辛烷-4-酮,然后还原为相应的
4-羟基化合物。得到的
4-羟基化合物去卤化并转化为相应的4-
氯或4-酮化合物。这些4-取代化合物可用于制备我们发明的其他化合物。分别从二苯并[5.1.0]辛-4-酮通过与二烷基
氨基丙基
格氏试剂反应,然后脱
水得到的氧化烯醇,或者从4-卤代-2,3,5,6-二苯并[5.1.0]
辛烷与二烷基
氨基丙基
格氏试剂反应制备的4-二烷基
氨基丙基二苯并[5.1.0]
辛烷化合物,制备出4-二烷基
氨基丙基二苯并[5.1.0]
辛烷化合物,这两种化合物作为抗抑郁剂使用。这两种二烷基
氨基丙基和二烷基
氨基丙基亚烯化合物通过去烷基化转化为相应的单烷基
氨基化合物。