749-13-3

Basic information

• Product Name: trifluperidol
• Synonyms: 4-fluoro-4-(4-hydroxy-4-(alpha,alpha,alpha-trifluoro-m-tolyl)piperidino)butyrophenone;trifluperidol;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
• CAS NO: 749-13-3
• Molecular Formula: C22H23F4NO2
• Molecular Weight: 409.4171328
• Mol File: 749-13-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 535.7°C at 760 mmHg
• Flash Point: 277.8°C
• Appearance: /
• Density: 1.2119 (estimate)
• Vapor Pressure: 2.62E-12mmHg at 25°C
• Refractive Index: 1.534
• PKA: 13.87±0.20(Predicted)
• CAS DataBase Reference: trifluperidol(CAS DataBase Reference)
• NIST Chemistry Reference: trifluperidol(749-13-3)
• EPA Substance Registry System: trifluperidol(749-13-3)

Safety Data

• Hazardous Substances Data: 749-13-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 749-13-3 differently. You can refer to the following data:
1. Antipsychotic.
2. 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.

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.

InChI:InChI=1/C22H23F4NO2/c23-19-9-3-16(4-10-19)20(28)2-1-13-27-14-11-21(29,12-15-27)17-5-7-18(8-6-17)22(24,25)26/h3-10,29H,1-2,11-15H2

Relevant articles and documents

Phenylbutanol derivatives

Butyrophenone derivatives having excellent psychotropic activity and represented by the formula, SPC1 Wherein A represents a single or double bond linkage; R1 represents a hydrogen atom or a C1 - C4 alkyl group; R2, which is present only in case A represents a single bond linkage, represents a hydrogen atom, or a hydroxyl, C1 - C4 alkyl, or C1 - C4 alkoxy group; R3 represents a hydrogen atom, or a piperidino, pyrrolidino, morpholino, furyl, thienyl, C1 - C4 alkylamino, benzylamino, unsubstituted or halogen-substituted phenyl group, etc.; and X represents a hydrogen or halogen atom, or a C1 - C4 alkyl, C1 - C4 alkoxy, or trifluoromethyl group, can be prepared by reducing a benzoylpropionamide derivative of the formula, SPC2 Wherein A, R1, R2, R3 and X have the same meanings as defined above, to a phenylbutanol derivative of the formula, SPC3