trifluperidol

Uses

Antipsychotic.

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.

Raw materials

Preparation Products