Preparation of n-alkylnorpavines via competitive n-dealkylation of quaternary pavines

Article abstract of DOI:10.3987/COM-96-7400

N-Alkyl quaternary pavine salts were converted into N-alkyl tertiary pavines by refluxing ethanolamine, via a competitive N-dealkylation mechanism. The following N-dealkylation order was observed: benzyl> allyl > Me > Et > ⁿPr ≥. ⁿBu. Further study indicated that N-alkyl- and N-acylpavines could be obtained from N-methyl tertiary pavines in a one-pot reaction (acid anhydride/ allyl bromide or alkyl halide, reflux). This finding provides an alternative method for preparing N-alkyl tertiary pavines .