Chemistry:Trifluperidol
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| Trade names | Triperidol |
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| Routes of administration | Oral |
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| Formula | C22H23F4NO2 |
| Molar mass | 409.425 g·mol−1 |
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Trifluperidol is a typical antipsychotic of the butyrophenone chemical class. It has general properties similar to those of haloperidol, but is considerably more potent by weight, and causes relatively more severe side effects, especially tardive dyskinesia and other extrapyramidal effects. It is used in the treatment of psychoses including mania and schizophrenia. It was discovered at Janssen Pharmaceutica in 1959.[1][2]
Synthesis
The Grignard 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).
See also
References
- ↑ "A controlled evaluation of Trifluperidol: a new potent psychopharmacologic agent". Current Therapeutic Research, Clinical and Experimental 5: 463–71. September 1963. PMID 14065098.
- ↑ "Trifluperidol: a butyrophenone derivative". The American Journal of Psychiatry 120 (5): 485–7. November 1963. doi:10.1176/ajp.120.5.485. PMID 14051242.
- ↑ GB895309 idem P. Adriaan J. Janssen, U.S. Patent 3,438,991 (1969 to Res Lab Dr C Janssen Nv).
- ↑ 彭响亮, CN patent 105439811 (2016 to Chengdu Zhongheng Huatie Technology Co Ltd).
- ↑ "Sila-Trifluperidol, a Silicon Analogue of the Dopamine (D 2 ) Receptor Antagonist Trifluperidol: Synthesis and Pharmacological Characterization". Organometallics 29 (7): 1652–1660. 12 April 2010. doi:10.1021/om901011t.
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