Progress in arylpiperazine synthesis by the catalytic amination reaction

Careful base and solvent optimization for catalytic amination is described. A Pd-catalyzed amination between some arylbromide and unprotected piperazine (1 equiv) was efficiently carried out with Pd/BINAP catalyst in a toluene–DBU solvent system, which is useful for the one-pot preparation of unsymm...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2002-12, Vol.10 (12), p.4023-4027
Main Authors: Torisawa, Yasuhiro, Nishi, Takao, Minamikawa, Jun-ichi
Format: Article
Language:English
Subjects:
Amination
Benzene Derivatives - chemical synthesis
Catalysis
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Indicators and Reagents
Naphthalenes - chemistry
Organic chemistry
Palladium - chemistry
Piperazines - chemical synthesis
Preparations and properties
Solvents - chemistry
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Summary:Careful base and solvent optimization for catalytic amination is described. A Pd-catalyzed amination between some arylbromide and unprotected piperazine (1 equiv) was efficiently carried out with Pd/BINAP catalyst in a toluene–DBU solvent system, which is useful for the one-pot preparation of unsymmetrical piperazine through amination and in-situ N-protection. Reaction with N-BOC-piperazine was also successful in toluene–DBU or more polar NMP with Cs 2CO 3 as a key base. No reports have previously reported such solvent and base optimization in arylpiperazine synthesis. Graphic
ISSN:0968-0896
1464-3391
DOI:10.1016/S0968-0896(02)00303-6