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Practical application of the palladium-catalyzed amination in phenylpiperazine synthesis: An efficient synthesis of a metabolite of the antipsychotic agent aripiprazole

✍ Scribed by Seiji Morita; Kazuyoshi Kitano; Jun Matsubara; Tadaaki Ohtani; Yoshikazu Kawano; Kenji Otsubo; Minoru Uchida

Book ID: 104208517
Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 513 KB
Volume: 54
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(98)00175-6

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✦ Synopsis

A metabolite of Aripiprazole (1), 7-[4-[4-(2,3-dichloro.4-hydroxyphenyl)-l-pipetazinyl]butoxy]-3,4-&~ydto-2(IH)-quinolino~ (2), was prepared by the coupling reaction of 1-(4-be, nzyloxy-2,3-dichlorophenyl)pipengine (11) with 7-(4-¢.hlombutoxy)-3,4-dihydm-2(1H)-quinolinone ( 16). The gelladium-catalyzed amination of contiguous tri-and tetra-substituted benzenes with piperazine derivatives was investigated. The key intmnedia~ 11 was ~y ~ using the palladium-catalyzed amination of phenyl bromide 15 with piperazine.

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