Copper-catalyzed amination of (bromophenyl)ethanolamine for a concise synthesis of aniline-containing analogues of NMDA NR2B antagonist ifenprodil

Cédric Bouteiller, Javier Becerril-Ortega, Patrice Marchand, Olivier Nicole, Louisa Barré, Alain Buisson, Cécile Perrio
Org. Biomol. Chem.. 2010-01-01; 8(5): 1111
DOI: 10.1039/b923255a

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1. Org Biomol Chem. 2010 Mar 7;8(5):1111-20. doi: 10.1039/b923255a. Epub 2010 Jan 6.

Copper-catalyzed amination of (bromophenyl)ethanolamine for a concise synthesis
of aniline-containing analogues of NMDA NR2B antagonist ifenprodil.

Bouteiller C(1), Becerril-Ortega J, Marchand P, Nicole O, Barré L, Buisson A,
Perrio C.

Author information:
(1)Laboratoire de Développements Méthodologiques en TEP, CEA/DSV/I2BM/CI-NAPS,
UMR 6232, CNRS, Université de Caen-Basse Normandie, Cyceron, Bd Henri Becquerel,
14074 Caen Cedex, France.

An operationally simple and concise synthesis of anilinoethanolamines, as NMDA
NR2B receptor antagonist ifenprodil analogues, was developed via a
copper-catalyzed amination of the corresponding bromoarene. Coupling was achieved
with linear primary alkylamines, alpha,omega-diamines, hexanolamine and
benzophenone imine, as well as with aqueous ammonia, in good yields using CuI and
N,N-diethylsalicylamide, 2,4-pentadione or 2-acetylcyclohexanone as catalytic
systems. Amination with ethylene diamine was efficient even in the absence of an
additive ligand, whereas no reaction occurred with ethanolamine whatever the
conditions used. The anilinoethanolamines were evaluated as NR2B receptor
antagonists in a functional inhibition assay. Aminoethylanilines displayed
inhibition effects close to that of ifenprodil.

DOI: 10.1039/b923255a
PMID: 20165802 [Indexed for MEDLINE]


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