Selective introduction of TMS groups in tryptamines: preparation of N1-TMS derivatives of tryptamines

Indolethylamines (tryptamines) with a primary animofunction react with Regisil under controlled conditions to yield a mono TMS derivative. Mass spectrometry to these derivatives shows that the TMS group is substituted on the indolic nitrogen (N1) 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.