![]() | |
Clinical data | |
---|---|
Trade names | Triperidol |
AHFS/Drugs.com | International Drug Names |
Routes of administration | Oral |
ATC code | |
Legal status | |
Legal status | |
Identifiers | |
| |
CAS Number |
|
PubChemCID | |
DrugBank |
|
ChemSpider |
|
UNII | |
ChEMBL | |
CompTox Dashboard(EPA) | |
Chemical and physical data | |
Formula | C22H23F4NO2 |
Molar mass | 409.425 g·mol−1 |
3D model (JSmol) | |
| |
|
Trifluperidol is atypical antipsychotic of thebutyrophenonechemical class. It has general properties similar to those ofhaloperidol, but is considerably more potent by weight, and causes relatively more severe side effects, especiallytardive dyskinesia and otherextrapyramidal effects. It is used in the treatment of psychoses includingmania andschizophrenia. It was discovered atJanssen Pharmaceutica in 1959.[2][3]
TheGrignard reaction between 1-benzyl-4-piperidone [3612-20-2] (1) and 3-bromobenzotrifluoride [401-78-5] (2) gives 1-benzyl-4-(3-(trifluoromethyl)phenyl)piperidin-4-ol,CID:12718203 (3).Catalytic hydrogenation removes the benzyl protecting group to give 4-[3-(trifluoromethyl)phenyl]-4-piperidinol [2249-28-7] (4). Alkylation with 4-Chloro-4'-fluorobutyrophenone [3874-54-2] (5) introduces the sidechain and hence completed the synthesis of Trifluperidol (6).