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Paper | Regular issue | Vol 29, No. 6, 1989, pp.1179-1183
Published online, 1st January, 1970
DOI: 10.3987/COM-89-4943
Tris-N,N’,N"’-(3’,4’,5’-trimethoxyphenethyl)-1,3,5-hexahydrotriazine, a Methylenemescaline Trimer: Characterization and Selective Cyclization to Anhalinine under Non-aqueous Conditions

Linda A. Chrisey and Arnold Brossi

*Natural Products Research Center, Department of Chemistry, University of New Brunswick, Bag Service #45222, Fredericton, New Brunswick, E3b 5A3, Canada


The product obtained from the reaction of mescaline with aqueous formaldehyde was assigned the hexahydrotriazine structure 3, on the basis of ms and 1H-nmr spectral data, and microanalysis. Reaction of 3 with hydrochloric acid in aqueous milieu afforded a mixture of anhalinine (2) and mescaline (1), however, exclusively 2 was obtained when the reaction was performed under non-aqueous conditions in glacial acetic acid or in dichloromethane with trifluoroacetic acid.