Mazapertine Synthesis
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Mazapertine (RWJ-37796) is an
antipsychotic Antipsychotics, also known as neuroleptics, are a class of Psychiatric medication, psychotropic medication primarily used to manage psychosis (including delusions, hallucinations, paranoia or disordered thought), principally in schizophrenia but ...
agent that was developed by
Johnson & Johnson Johnson & Johnson (J&J) is an American multinational corporation founded in 1886 that develops medical devices, pharmaceuticals, and consumer packaged goods. Its common stock is a component of the Dow Jones Industrial Average and the company i ...
but never marketed. It exerts its pharmacological effect through affinity for dopamine D2, serotonin 5-HT1A, and α1-adrenergic receptors. Mazapertine is safe and well tolerated when administered orally. Analogs of mazapertine with conformational restriction have been prepared and have greater affinity for the 5-HT1A receptor.


Synthesis

Alkylation of
2-Nitrophenol Nitrophenols are compounds of the formula HOC6H5−x(NO2)x. The conjugate bases are called nitrophenolates. Nitrophenols are more acidic than phenol itself. Mono-nitrophenols with the formula HOC6H4NO2. Three isomeric nitrophenols exist: ...
8-75-5(1) with isopropyl bromide gives 2-isopropoxynitrobenzene 8753-50-3(2). Catalytic hydrogenation of nitro group gives 2-isopropoxyaniline 9026-74-2(3). Intermolecular ring formation of this aniline with nornitrogen mustard 34-22-5yields 1-(2-isopropoxyphenyl)piperazine 4013-91-1(4). Amide formation of 3-(chloromethyl)benzoyl chloride 3024-77-1(5) with piperidine gives 1- -(chloromethyl)benzoyliperidine 48583-64-6(6). Ex 1: The last step is the convergent synthesis between the above two arms of the synthesis to afford the alkylation product mazapertine (7).


References

Antipsychotics 1-Piperidinyl compounds Piperazines Phenol ethers Isopropyl compounds Carboxamides {{Nervous-system-drug-stub