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trifluperidol

CAS No.
749-13-3
Chemical Name:
trifluperidol
Synonyms
trifluperidol;trifluperidol USP/EP/BP;1-(4-fluorophenyl)-4-[4-hydroxy-4-[3-(trifluoromethyl)phenyl]-1-piperidyl]butan-1-one;4-fluoro-4-(4-hydroxy-4-(alpha,alpha,alpha-trifluoro-m-tolyl)piperidino)butyrophenone;1-(4-fluorophenyl)-4-[4-hydroxy-4-[3-(trifluoromethyl)phenyl]piperidin-1-yl]butan-1-one
CBNumber:
CB1875676
Molecular Formula:
C22H23F4NO2
Molecular Weight:
409.42
MDL Number:
MFCD00600324
MOL File:
749-13-3.mol
MSDS File:
SDS
Last updated:2023-05-04 17:34:42

trifluperidol Properties

Boiling point 515.9±50.0 °C(Predicted)
Density 1.2119 (estimate)
pka 13.87±0.20(Predicted)
CAS DataBase Reference 749-13-3
FDA UNII R8869Q7R8I
ATC code N05AD02

trifluperidol Chemical Properties,Uses,Production

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).
Synthesis_749-13-3_1
The 4'-chloro-4-fluorobutirophenone (6.3.4) needed for this is synthesized by the acylation of fluorobenzene using 4-chlorobutyric acid chloride.
Synthesis_749-13-3_2

trifluperidol Preparation Products And Raw materials

Raw materials

Preparation Products

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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 trifluperidol trifluperidol USP/EP/BP 749-13-3 C22H23F4NO2