Preparation of n-alkylnorpavines via competitive n-dealkylation of quaternary pavines
Journal
Heterocycles
Journal Volume
43
Journal Issue
7
Pages
1403-1414
Date Issued
1996
Author(s)
Tung K.-T.
Abstract
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 .
Type
journal article