Skip to main content

Practical Synthesis of 1-(7-Fluoro-naphthalen-1-yl)piperazine Hydrochloride

Buy Article:

$55.00 plus tax (Refund Policy)

A practical and scalable preparation of 1-(7-fluoronaphthalen-1-yl)-piperazine hydrochloride (1) is reported. The original route for the synthesis of this compound involved the use of 1-amino-7-fluoronaphthalene and bis(2-chloroethyl)amine hydrochloride, two highly toxic compounds. A new protocol has been developed that employs a palladium-catalyzed Buchwald-Hartwig cross-coupling reaction between 1-Boc-piperazine and 1-bromo-7-fluoronaphthalene followed by piperazine deprotection with HCl gas. In addition, an efficient palladium removal protocol allowed for the preparation of the target molecule with less than 20 ppm of this metal. This methodology has been successfully implemented to produce multigram quantities of 1 with excellent purity and low palladium content.
No Reference information available - sign in for access.
No Citation information available - sign in for access.
No Supplementary Data.
No Article Media
No Metrics

Keywords: Buchwald-Hartwig coupling; fluoronaphthalene; palladium catalyzed cross-coupling; piperazine

Document Type: Research Article

Affiliations: 1: Research API, Pfizer Global Research and Development, Groton, Connecticut, USA 2: Separation Sciences, Pfizer Global Research and Development, Groton, Connecticut, USA 3: Research API, Pfizer Global Research and Development, Ann Arbor, Michigan, USA 4: Supply Chain API, Pfizer Global Research and Development, Ann Arbor, Michigan, USA

Publication date: 2008-01-01

  • Access Key
  • Free content
  • Partial Free content
  • New content
  • Open access content
  • Partial Open access content
  • Subscribed content
  • Partial Subscribed content
  • Free trial content
Cookie Policy
X
Cookie Policy
Ingenta Connect website makes use of cookies so as to keep track of data that you have filled in. I am Happy with this Find out more