Tiflorex, formerly known as flutiorex, is a stimulant amphetamine. Its most pronounced effect is in suppression of appetite; it has little effect on pulse rate, sleep, or mood. It was found to be twice as potent an anorectic as

fenfluramine Fenfluramine, sold under the brand name Fintepla, is a serotonergic medication used for the treatment of seizures associated with Dravet syndrome and Lennox–Gastaut syndrome.https://www.accessdata.fda.gov/drugsatfda_docs/label/2022/212102s003lb ...

. SL 72.340-d was cited to be 4x the anorectant potency of fenfluramine (ED50=1.4 mg/kg vs 5.6 mg/kg).

Synthesis

The

Rosenmund reduction The Rosenmund reduction is a hydrogenation process in which an acyl chloride is selectively reduced to an aldehyde. The reaction was named after Karl Wilhelm Rosenmund, who first reported it in 1918. The reaction, a hydrogenolysis, is cataly ...

of 3-(trifluoromethylthio)benzoyl chloride 1748-28-8(1) gave 3-((trifluoromethyl)thio)benzaldehyde 1748-27-7(2).

Henry reaction The Henry reaction is a classic carbon–carbon bond formation reaction in organic chemistry. Discovered in 1895 by the Belgian chemist Louis Henry (1834–1913), it is the combination of a nitroalkane and an aldehyde or ketone in the presence ...

with nitroethane led to 1-(2-nitroprop-1-en-1-yl)-3- trifluoromethyl)sulfanylenzene 76242-84-5(3). With the aid of iron catalyst in concentrated HCl acid there occurred FGI into 1-(3'-trifluoromethylthiophenyl)-2-propanone
CID:21325269
(4'). Reductive amination with ethylamine and formic acid as the reductant completed the synthesis of tiflorex (5).

References

Anorectics Trifluoromethyl compounds Substituted amphetamines Thioethers {{nervous-system-drug-stub