| Identification | Back Directory | [Name]
trifluperidol | [CAS]
749-13-3 | [Synonyms]
trifluperidol
trifluperidol USP/EP/BP
4-fluoro-4-(4-hydroxy-4-(alpha,alpha,alpha-trifluoro-m-tolyl)piperidino)butyrophenone
1-(4-fluorophenyl)-4-[4-hydroxy-4-[3-(trifluoromethyl)phenyl]-1-piperidyl]butan-1-one
1-(4-fluorophenyl)-4-[4-hydroxy-4-[3-(trifluoromethyl)phenyl]piperidin-1-yl]butan-1-one | [Molecular Formula]
C22H23F4NO2 | [MDL Number]
MFCD00600324 | [MOL File]
749-13-3.mol | [Molecular Weight]
409.417 |
| Hazard Information | Back Directory | [Uses]
Antipsychotic. | [Brand name]
Triperidol (Ortho-McNeil). | [Definition]
ChEBI: Trifluperidol is an aromatic ketone. | [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.
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| Safety Data | Back Directory | [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. |
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