A note on the synthesis and gas chromatographic-mass spectrometric properties of N-(Trimethylsilyl)-acetates of amphetamine and analogs

Article abstract of DOI:10.1093/chromsci/17.6.350

Amphetamine, some N-alkyl homologs, and ring-methoxylated analogs were each treated with a slight excess of trimethylsilylketene in dimethoxyethane or carbon tetrachloride. N-(trimethylsilyl)acetate derivatives formed almost quantitatively within a few minutes at room temperature; this was ascertained by nuclear magnetic resonance and infrared studies on the compounds. The N-(trimethylsilyl)acetate derivatives decomposed to varying extents on GC; some were relatively stable with barely detectable decomposition, while others decomposed extensively to the corresponding N-acetates. The N-(trimethylsilyl)acetates were converted quantitatively to the corresponding N-acetates by the action of aqueous hydrochloric acid.