Pirlindole, sold under the brand names Lifril and Pyrazidol, is mainly a reversible inhibitor of monoamine oxidase A (RIMA) and secondly a serotonin–norepinephrine reuptake inhibitor (SNRI) which was developed and is used in Russia as an antidepressant.
Synthesis
The Fischer indole synthesis between
p-Tolylhydrazine Hydrochloride 637-60-5 (
1) and 1,2-Cyclohexanedione 765-87-7 (
2) gives 6-methyl-2,3,4,9-tetrahydrocarbazol-1-one 3449-48-7 (
3). Imine formation with
ethanolamine 141-43-5 (
4) gives
CID:2838578 (
5). Halogenation with phosphorus oxychloride gives (
6).
Intramolcular alkylation with the indole nitrogen resulted in Dehydropirlindole 75804-32-9 (
7). Reduction of the imine with sodium borohydride completes the synthesis of pirlindole (
8).
See also
