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| Names | |
|---|---|
| Preferred IUPAC name (Piperidin-1-yl){3-[(4-{2-[(propan-2-yl)oxy]phenyl}piperazin-1-yl)methyl]phenyl}methanone | |
| Other names RWJ-37796 | |
| Identifiers | |
3D model (JSmol) | |
| ChEMBL | |
| ChemSpider | |
| UNII | |
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| Properties | |
| C26H35N3O2 | |
| Molar mass | 421.585 g·mol−1 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Mazapertine (RWJ-37796) is anantipsychotic agent that was developed byJohnson & Johnson but never marketed. It exerts its pharmacological effect through affinity fordopamine D2,serotonin 5-HT1A, andα1-adrenergic receptors.[1]
Mazapertine is safe and well tolerated when administered orally.[2]
Analogs of mazapertine withconformational restriction have been prepared and have greater affinity for the5-HT1A receptor.[3]
The laboratory synthesis of mazapertine has been reported.[4][5][6] It begins withalkylation of2-nitrophenol (1) withisopropyl bromide to give 2-isopropoxynitrobenzene (2).Catalytic hydrogenation of nitro group gives 2-isopropoxyaniline (3). Intermolecular ring formation of this aniline with bis(2-chloroethyl)amine yields 1-(2-isopropoxyphenyl)piperazine (4). Separately, amide formation of 3-(chloromethyl)benzoyl chloride (5) with piperidine gives 1-[3-(chloromethyl)benzoyl]piperidine (6). The last step is the convergent synthesis between the above two arms of the synthesis to afford the alkylation product mazapertine (7).
