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Synthesis of Bis[di(2‐pyridyl)methyl]amine (BDPMA) by a Novel One‐Pot Multi‐Step Reductive Amination with Molecular Sieves and Zn/ i PrOH
Author(s) -
Renz Michael,
Hemmert Catherine,
Meunier Bernard
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199807)1998:7<1271::aid-ejoc1271>3.0.co;2-q
Subject(s) - chemistry , reductive amination , methylamine , molecular sieve , amine gas treating , imine , zinc , organic chemistry , acetic acid , amination , ketone , medicinal chemistry , catalysis , combinatorial chemistry
Bis[di(2‐pyridyl)methyl]amine (BDPMA) has been syn‐thesized by refluxing di‐2‐pyridyl ketone and di‐(2‐pyridyl)methylamine in isopropanol in the presence of molecular sieves and acetic acid and subsequent reduction with zinc dust. The established methods for reductive amination, i.e. NaBH 3 CN, NaBH(OAc) 3 and NaBH 4 , failed in the synthesis of BDPMA due to a disfavored equilibrium towards the imine formation and therefore long reaction times were required, involving side reactions. The presented method can be used on large‐scales and tolerates aromatic heterocycles as functional groups.