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Synthesis 1995; 1995(7): 766-768
DOI: 10.1055/s-1995-4013
short paper
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A Novel Synthesis of the Enantiomers of an Antihistamine Drug by Piperazine Formation from a Primary Amine

C. J. Opalka, T. E. D’Ambra* , J. J. Faccone, G. Bodson, E. Cossement
  • *Albany Molecular Research, Inc., 21 Corporate Circle, Albany, New York 12203 USA, Fax +1(518)4640289
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Publikationsdatum:
31. Dezember 2000 (online)

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An enantioselective synthesis of each enantiomer of the antihistamine drug 2(2-{4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl}ethoxy)acetic acid dihydrochloride (1) is described, involving the preparation of the benzhydrylpiperazine portion of the molecule from reaction of each enantiomer of 4-chlorobenzhydrylamine with N,N-bis(2-chloroethyl)-4-methylbenzenesulfonamide. A modification of standard toluenesulfonamide deprotection with hydrogen bromide in acetic acid was introduced, substituting 4-hydroxybenzoic acid for phenol.

enantiospecific synthesis of piperazine from primary amine - cetirizine