- Practical application of the palladium-catalyzed amination in phenylpiperazine synthesis: An efficient synthesis of a metabolite of the antipsychotic agent aripiprazole
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A metabolite of Aripiprazole (1), 7-[4-[4-(2,3-dichloro-4- hydroxyphenyl)-1-piperaziyl]butoxy]-3,4-dihydro-2(1H)-quinolinone (2), was prepared by the coupling reaction of 1-(4-benzyloxy-2,3-dichlorophenyl) piperazine (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 was efficiently prepared using the palladium-catalyzed amination of phenyl bromide 15 with piperazine.
- Morita, Seiji,Kitano, Kazuyoshi,Matsubara, Jun,Ohtani, Tadaaki,Kawano, Yoshikazu,Otsubo, Kenji,Uchida, Minoru
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p. 4811 - 4818
(2007/10/03)
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- Hydroxylation of Nitroarenes with Alkyl Hydroperoxide Anions via Vicarious Nucleophilic Substitution of Hydrogen
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Rhone-Poulenc Polska Ltd., ul. Grzybowska 80/82, 00-844 Warszawa, Poland Garbo- and heterocyclic nitroarenes react with anions of tert-butyl and cumyl hydroperoxides in the presence of strong bases to form substituted o- and p-nitrophenols. The reaction usually proceeds in high yields and is of practical value as a method of synthesis and manufacturing of nitrophenols. Orientation of the hydroxylation can be controlled to a substantial extent by selection of the proper conditions. Basic mechanistic features of this process were clarified.
- Makosza, Mieczyslaw,Sienkiewicz, Krzysztof
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p. 4199 - 4208
(2007/10/03)
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- 6,7-dihalomelatonins
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6,7-Dichloromelatonin and related compounds are ovulation inhibitors of the formula STR1 wherein R and R1 are individually F or Cl, R2 is C1-3 alkyl, including methyl, ethyl, n-propyl and isopropyl, and R3 is H or methyl.
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