Clomacran

Clomacran is an antipsychotic drug of the dihydroacridine class, developed in the 1970s by the pharmaceutical company Smith, Kline & French under the brand names Devryl and Olaxin.
It was used to treat schizophrenia in the 1970s. It was withdrawn from the market in the UK, due to liver toxicity, in 1982.

Synthesis

Clomacran can be synthesized beginning with 2-chloroacridone which is reacted with a Grignard reagent derived from 3-chloro-N,''N''-dimethylpropylamine to afford the tertiary carbinol. Dehydration by means of acid or simply heat gives the corresponding olefin. Catalytic reduction completes the synthesis of clomacran.