Synthesis of the psychotherapeutic drug, amitriptyline (XI), has been accomplished heretofore in the main by way of simple Grignard coupling of y-dimethylaminopropylchloride with 5H-dibenao [a, d]-10,-1 1-dihydrocyclohepten-&one followed by dehydration.'Recently we showed2 that the carbinol (I), derived from 57-dibenzo [a, d 1-10, l I-dihydrocyclohepten- 5-one (IY) and cyclopropylmagnesium bromide, rearranges quantitatively to 5-(y- ...
![11-prop-2-enylidene-5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulene Structure](https://image.chemsrc.com/caspic/440/24755-73-5.png)