Selective Introduction of TMS Groups in Tryptamines: Preparation of N1-TMS Derivatives of Tryptamines

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Abstract
Indolethylamines (tryptamines) with a primary aminofunction react with Regisil under controlled conditions to yield a mono TMS derivative. Mass spectrometry of these derivatives shows that the TMS group is substituted on the indolic nitrogen (N-1) and not the primary amino nitrogen. This is confirmed by converting these compounds to their isothiocyanate derivatives. The GC and GC-MS data of some typical compounds are presented.