Trifluperidol is a

typical antipsychotic Typical antipsychotics (also known as major tranquilizers, and first generation antipsychotics) are a class of antipsychotic drugs first developed in the 1950s and used to treat psychosis (in particular, schizophrenia). Typical antipsychotics m ...

of the

butyrophenone Butyrophenone is an organic compound with the formula C6H5C(O)C3H7. It is a colorless liquid. The butyrophenone structure—a ketone flanked by a phenyl ring and a butyl chain—forms the basis for many other chemicals containing various subst ...

chemical class Chemical classification systems attempt to classify elements or compounds according to certain chemical functional or structural properties. Whereas the structural properties are largely intrinsic, functional properties and the derived classi ...

. It has general properties similar to those of

haloperidol Haloperidol, sold under the brand name Haldol among others, is a typical antipsychotic medication. Haloperidol is used in the treatment of schizophrenia, tics in Tourette syndrome, mania in bipolar disorder, delirium, agitation, acute psychos ...

, but is considerably more potent by weight, and causes relatively more severe side effects, especially

tardive dyskinesia Tardive dyskinesia (TD) is an iatrogenic disorder that results in involuntary repetitive body movements, which may include grimacing, sticking out the tongue or smacking the lips, which occurs following treatment with medication. Additional mo ...

and other extrapyramidal effects. It is used in the treatment of psychoses including

mania Mania, also known as manic syndrome, is a Psychiatry, psychiatric Abnormality (behavior), behavioral syndrome defined as a state of Abnormality (behavior), abnormally elevated arousal, affect (psychology), affect, and energy level. During a mani ...

and

schizophrenia Schizophrenia () is a mental disorder characterized variously by hallucinations (typically, Auditory hallucination#Schizophrenia, hearing voices), delusions, thought disorder, disorganized thinking and behavior, and Reduced affect display, f ...

. It was discovered at

Janssen Pharmaceutica Johnson & Johnson Innovative Medicine (formerly Janssen Pharmaceuticals) is a Belgian pharmaceutical company headquartered in Beerse, Belgium, and wholly owned by Johnson & Johnson. It was founded in 1953 by Paul Janssen. In 1961, Janssen Ph ...

in 1959.

Synthesis

The

Grignard reaction The Grignard reaction () is an organometallic chemical reaction in which, according to the classical definition, carbon alkyl, allyl, vinyl, or aryl magnesium halides (Grignard reagent) are added to the carbonyl groups of either an aldehyde or ...

between 1-benzyl-4-piperidone 612-20-2(1) and 3-bromobenzotrifluoride 01-78-5(2) gives 1-benzyl-4-(3-(trifluoromethyl)phenyl)piperidin-4-ol
CID:12718203
(3).

Catalytic hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate organic ...

removes the benzyl protecting group to give 4- -(trifluoromethyl)phenyl4-piperidinol 249-28-7(4). Alkylation with 4-Chloro-4'-fluorobutyrophenone 874-54-2(5) introduces the sidechain and hence completed the synthesis of Trifluperidol (6).

References

{{Dopaminergics 4-Phenylpiperidines Tertiary alcohols Aromatic ketones Belgian inventions Butyrophenone antipsychotics Janssen Pharmaceutica Trifluoromethyl compounds Typical antipsychotics 4-Fluorophenyl compounds

Synthesis

See also

References