A Precautionary Note Regarding Derivatization Of Secondary Amines With Dialkyeacetals Of Formamide Other Than The Diethyl Derivative A Correction

Abstract

Abstract In an earlier communication we reported GC-MS studios on the reaction products of secondary amino tricyclics and dimethylformamide. 1 The diethyl acctal reaction products were identified as N-ethyl derivatives on the basis of mass spectroscopic analysis. In a follow-up study, we reported the same reaction products were formed from other DMF-dialkyl acetals, such as dimethyl and dipropyl acetals. 2 In view of this unusual reaction we reinvestigated the structure of the reaction products utilizing alternative spectroscopic methods, viz. NMR and IR, and present a correction to our earlier work ()Desipramine (1 mg) was heated with DMF-diethyl acetal (100 μ 1) at 80°C. for 15 min. The product: was dissolved in ethyl acetate (5 ml), extracted into 1 ml of 0.5 N HCl and back extracted into ethyl acetate at pH 11.0. The organic extract was dried over anhydrous sodium sulfate and evaporated to dryness under nitrogen. The resulting residue was used directly in the NMR and IR studies.