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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

S. Morita, Kazuyoshi Kitano, J. Matsubara, Tadaaki Ohtani, Y. Kawano, K. Otsubo, M. Uchida
Published 1998 · Chemistry

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A metabolite of Aripiprazole (1), 7-[4-[4-(2,3-dichloro-4-hydroxyphenyl)-1-piperazinyl]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.
This paper references
10.1021/JA971583O
Palladium-Catalyzed Coupling of Optically Active Amines with Aryl Bromides
Seble H. Wagaw (1997)
10.1016/0040-4020(96)00266-9
Intramolecular palladium-catalyzed aryl amination and aryl amidation
J. Wolfe (1996)
10.1016/0040-4039(95)00605-C
Palladium-catalyzed synthesis of arylamines from aryl halides. Mechanistic studies lead to coupling in the absence of tin reagents
J. Louie (1995)
10.1021/JM00393A020
Effects of [(N-alkyl-1,3-dioxo-1H,3H-isoindolin-5-yl)oxy]alkanoic acids, [(N-alkyl-1-oxo-1H,3H-isoindolin-5-yl)oxy]butanoic acids, and related derivatives on chloride influx in primary astroglial cultures.
S. Wyrick (1987)
10.1021/JO951844H
PALLADIUM-CATALYZED AMINATION OF ARYL IODIDES
J. Wolfe (1996)
10.1248/CPB.35.3215
Studies on uricosuric diuretics. II. 6,7-Dichloro-4-nitro-, 6,7-dichloro-4-sulfamoyl- and 6,7-dichloro-4-acyl-2,3-dihydrobenzofuran-2-carboxylic acids.
H. Harada (1987)
10.1021/JO970876X
Room Temperature Catalytic Amination of Aryl Iodides
J. Wolfe (1997)
10.1016/S0040-4039(97)01465-2
An Ammonia Equivalent for the Palladium-Catalyzed Amination of Aryl Halides and Triflates
J. Wolfe (1997)
10.1021/JO9622946
Palladium-Catalyzed Amination of Aryl Bromides: Use of Phosphinoether Ligands for the Efficient Coupling of Acyclic Secondary Amines
J. Marcoux (1997)
10.1002/ANIE.199513481
A Simple Catalytic Method for the Conversion of Aryl Bromides to Arylamines
A. Guram (1995)
10.1021/JO9612739
The Synthesis of Aminopyridines: A Method Employing Palladium-Catalyzed Carbon-Nitrogen Bond Formation.
Seble H. Wagaw (1996)
10.1016/s0040-4039(97)01464-0
An Improved Method for the Palladium-Catalyzed Amination of Aryl Triflates
J. Ahman (1997)
10.1021/JO961930X
Palladium-Catalyzed Amination of Aryl Triflates and Importance of Triflate Addition Rate
J. Louie (1997)
10.1021/JA960937T
A Second-Generation Catalyst for Aryl Halide Amination: Mixed Secondary Amines from Aryl Halides and Primary Amines Catalyzed by (DPPF)PdCl2
M. Driver (1996)
10.1016/S0040-4039(97)01463-9
IMPROVED FUNCTIONAL GROUP COMPATIBILITY IN THE PALLADIUM-CATALYZED AMINATION OF ARYL BROMIDES
J. Wolfe (1997)
10.1021/JO961915S
Palladium-Catalyzed Amination of Aryl Triflates
J. Wolfe (1997)
10.1021/JA9608306
An Improved Catalyst System for Aromatic Carbon−Nitrogen Bond Formation: The Possible Involvement of Bis(Phosphine) Palladium Complexes as Key Intermediates
J. Wolfe (1996)



This paper is referenced by
10.1016/J.EJPHAR.2006.07.008
Aripiprazole and its human metabolite are partial agonists at the human dopamine D2 receptor, but the rodent metabolite displays antagonist properties.
M. Wood (2006)
10.1016/j.bmc.2010.07.034
Discovery of {1-[4-(2-{hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl}-1H-benzimidazol-1-yl)piperidin-1-yl]cyclooctyl}methanol, systemically potent novel non-peptide agonist of nociceptin/orphanin FQ receptor as analgesic for the treatment of neuropathic pain: design, synthesis, and structure-activity relat
S. Hayashi (2010)
10.1002/9781118309872.CH3
Selected Applications of Pd‐ and Cu‐Catalyzed Carbon–Heteroatom Cross‐Coupling Reactions in the Pharmaceutical Industry
Jingjun Yin (2012)
10.1002/CJOC.201300427
Catalytic Mechanism of Cytochrome P450 2D6 for 4‐Hydroxylation of Aripiprazole: A QM/MM Study
Rongwei Shi (2013)
10.1002/9781118309872.CH1
Transition Metal Catalysis in the Pharmaceutical Industry
C. Busacca (2012)
10.1016/S1460-1567(07)80063-8
Chapter 14 Industrial scale palladium chemistry
Marudai Balasubramanian (2007)
10.1016/S0022-328X(98)01054-7
Palladium-catalyzed amination of aryl halides and sulfonates
B. Yang (1999)
10.1039/A903369F
Amines and amides
M. North (1998)
10.1002/CHIN.199831165
Practical Application of the Palladium-Catalyzed Amination in Phenylpiperazine Synthesis: An Efficient Synthesis of a Metabolite of the Antipsychotic Agent Aripiprazole.
S. Morita (1998)
10.1016/J.TETLET.2004.10.170
Mercury chloride assisted cyclization toward benzimidazoles by focused microwave irradiation
Y. Su (2005)
10.1007/3-540-45313-X_5
Practical Palladium Catalysts for C-N and C-O Bond Formation
Alexander R. Muci (2002)
10.1016/S0040-4039(99)01487-2
Liquid-phase synthesis of 2-(alkylthio) benzimidazoles
Chih-Ming Yeh (1999)
10.1016/S0040-4039(03)00453-2
Solid-phase synthesis of benzimidazole libraries biased for RNA targets
D. Vourloumis (2003)
10.1016/J.BMCL.2006.11.083
Potent, selective, and orally active adenosine A2A receptor antagonists: arylpiperazine derivatives of pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines.
B. Neustadt (2007)
10.1016/S0960-894X(99)00384-4
Synthesis of new (benzimidazolyl)piperazines with affinity for the 5-HT1A receptor via Pd(0) amination of bromobenzimidazoles.
M. López-Rodríguez (1999)
10.1016/S0040-4020(99)00668-7
Recent synthetic advances in the nucleophilic amination of benzenes
A. Belfield (1999)
10.1016/S0968-0896(02)00303-6
Progress in arylpiperazine synthesis by the catalytic amination reaction.
Y. Torisawa (2002)
10.1016/S0040-4039(02)00013-8
Soluble polymer-supported synthesis of 2-(arylamino)benzimidazoles
Cheng-Yi Wu (2002)
10.1002/JLCR.1017
Synthesis of multi‐labeled [14C]Aripiprazole
S. Bonacorsi (2006)
10.1007/s11030-010-9244-7
Scaffold-directed and traceless synthesis of tricyclic quinoxalinone imidazoles under microwave irradiation
Suman Thummanagoti (2010)
10.1016/S0040-4020(00)00225-8
Pd(0) Amination of Benzimidazoles as an Efficient Method towards New (Benzimidazolyl)piperazines with High Affinity for the 5-HT1A Receptor
María L. López-Rodríguez (2000)
10.1016/S0040-4039(02)02384-5
Palladium-catalyzed amination of 3-bromo-4-fluoro-acetophenone
L. Sun (2002)
10.1016/S0960-894X(02)00857-0
Synthetic study on the unique dimeric arylpiperazine: access to the minor contaminant of aripiprazole.
Y. Torisawa (2003)
10.1021/jm300482h
Molecular determinants of selectivity and efficacy at the dopamine D3 receptor.
A. Newman (2012)
10.1016/S0040-4020(02)00076-5
Palladium-catalysed reactions of aryl halides with soft, non-organometallic nucleophiles
Damien Prim (2002)
10.1016/S0960-894X(02)00058-6
Soluble polymer-supported synthesis of benzodiazepinones.
C. Y. Wu (2002)
10.1016/S0040-4020(02)00165-5
The mono-functionalization of symmetrical polyamines
J. A. Bender (2002)
10.1016/S0040-4020(02)00750-0
Nickel-catalysed selective N-arylation or N,N′-diarylation of secondary diamines
E. Brenner (2002)
10.1016/S0040-4039(99)01276-9
HIGH-THROUGHPUT COMBINATORIAL SYNTHESIS OF SUBSTITUTED BENZIMIDAZOLONES
Pi-Chi Pan (1999)
10.1002/cmdc.201300474
Binding Kinetics of ZM241385 Derivatives at the Human Adenosine A2A Receptor
D. Guo (2014)
Nouvelles phenylpiperidines/piperazines disubstitues utilisees comme modulateurs de neurotransmission de la dopamine
Clas Sonesson (2005)
10.1021/OL050848Y
Synthesis of biologically active amines via rhodium-bisphosphite-catalyzed hydroaminomethylation.
J. R. Briggs (2005)
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