Practical application of the palladium-catalyzed amination in phenylpiperazine synthesis: An efficient synthesis of a metabolite of the antipsychotic agent aripiprazole
A hydroxylated metabolite 2 of Aripiprazole (1) was prepared by the coupling reaction of 11 with 7-(4-chlorobutoxy)-3,4-dihydro-2(1H)-quinolinone (16). The palladium-catalyzed amination of contiguous tri- and tetra-substituted benzenes with piperazine derivatives was investigated. The key intermediate 11 and 2,3-dichlorophenylpiperazine (13a) were efficiently prepared using the palladium-catalyzed amination of phenyl bromides 15 and 12a with piperazine, respectively.
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