Uses
Trifluperidol is a powerful antipsychotic drug. It enhances the action of soporifics,
narcotics, and analgesics. It also possesses anticonvulsant and antiemetic action.
It is used in psychoses accompanied by motor and mental excitement, in prolonged attacks
of recurrent schizophrenia, in cases accompanied by severe depression and delirium, and in alcoholic psychoses. It surpasses other neuroleptics in terms of its ability to stop minor manic
excitement.
Definition
ChEBI: Trifluperidol is an aromatic ketone.
brand name
Triperidol (Ortho-McNeil).
Safety Profile
Poison by ingestion,
subcutaneous, and intraperitoneal routes. An
experimental teratogen. Experimental
reproductive effects. When heated to
decomposition it emits very toxic fumes of
Fand NOx. See also FLUORIDES and
TRIFLUPERIDOL HYDROCHLORIDE.
Synthesis
Trifluperidol, 4-[4-(α,α,α-trifluoro-m-tolyl)-4-hydroxypiperidino]-4′- fluorobutirophenone (6.3.3), is synthesized by reacting 1-benzyl-4-piperidone (3.1.48) with a Grignard reagent prepared from 1-trifluoromethyl-3-bromobenzene and magnesium that forms 1-benzyl-4-hydroxy-4-(3-trifluoromethylphenyl)piperidine (6.3.1), the reduction of which with hydrogen in the presence of a palladium on carbon catalyst removes the benzyl protecting group giving 4-hydroxy-4-(3-trifluoromethylphenyl)piperidine (6.3.2). Alkylation of the nitrogen atom of the last by ω–chloro-4-fluorobutyrophenone gives trifluperidol (6.3.3).
The 4'-chloro-4-fluorobutirophenone (6.3.4) needed for this is synthesized by the acylation of fluorobenzene using 4-chlorobutyric acid chloride.
