Chemistry:Clocinizine
From HandWiki
Short description: Chemical compound
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| Clinical data | |
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| Trade names | Senioral (with PPA) |
| AHFS/Drugs.com | International Drug Names |
| Routes of administration | By mouth |
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| Formula | C26H27ClN2 |
| Molar mass | 402.97 g·mol−1 |
| 3D model (JSmol) | |
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Clocinizine is a first-generation antihistamine of the diphenylmethylpiperazine class. It is marketed in Spain in combination with phenylpropanolamine under the brand name Senioral.[1]
Synthesis
The reduction of 4-Chlorobenzophenone [134-85-0] (1) with NBH gives 4-Chlorobenzhydrol [119-56-2] (2). Halogenation of the alcohol in muriatic acid afforded 4-Chlorobenzhydryl chloride [134-83-8] (3). Alkylation with one equivalent of piperazine gives 1-(4-Chlorobenzhydryl)piperazine [303-26-4] (4). Alkylation of the remaining nitrogen with Cinnamyl Bromide [4392-24-9] (5) completed the synthesis of Clocinizine (6).
References
- ↑ "List of Common Antihistamines + Uses & Side Effects". Drugs.com. September 2022. https://www.drugs.com/international/clocinizine.html.
- ↑ "Efficient synthesis of antihistamines clocinizine and chlorcyclizine.". Medicinal Chemistry Research 21 (4): 538–541. April 2012. doi:10.1007/s00044-011-9556-x.
- ↑ Kato H, Kurata S, "Antiarrhythmic piperazine derivs prepn - from benzhydrylpiperazine cinnamaldehyde by leuckart reaction", DE patent 2220242, issued 1972, assigned to Hokuriku Pharmaceutical
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