A short and efficient synthesis of N-aryl- and N-heteroaryl-N′- (arylalkyl)piperazines

Dirk Michalik, Kamal Kumar, Alexander Zapf, Annegret Tillack, Michael Arlt, Timo Heinrich, Matthias Beller

Research output: Contribution to journalArticlepeer-review

33 Scopus citations


A new synthesis of N-aryl- and N-heteroaryl-N′-(arylalkyl) piperazines using palladium-catalyzed amination of aryl bromides and heteroaryl chlorides with mono N-benzyl- or N-(arylethyl)piperazines is reported. Most coupling processes proceed in high yield and good selectivity using either diadamantyl-n-butylphosphine (1), 2-(dicyclohexylphosphino)-2′-(N,N- dimethylamino)biphenyl (2), or 2-(di-tert-butylphosphino)biphenyl (3) as ligand. Applying an automated parallel synthesizer the preparation of a small library of potentially bioactive compounds is easily achieved.

Original languageEnglish
Pages (from-to)2057-2061
Number of pages5
JournalTetrahedron Letters
Issue number10
StatePublished - 1 Mar 2004
Externally publishedYes


  • Aminations
  • Palladium
  • Piperazine


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