The Vespiary

The Hive => Tryptamine Chemistry => Topic started by: SPISSHAK on June 21, 2002, 08:18:00 AM

Title: dialkyltryptamine synthesis through alkyliodides.
Post by: SPISSHAK on June 21, 2002, 08:18:00 AM

I read shulgin`s book TIHKAL and notice when he alkylates typtamine with ethyl bromide.
And eliminates alkylbromides from the quarternary ammonium halides with diazabicyclooctanes.
Why doesn`t the indole nitrogen get alkylated???
Call me stupid about tryptamine chemistry I don`t care...

Title: indole nitrogen is not an amine
Post by: Lilienthal on June 21, 2002, 04:09:00 PM

Because the indole nitrogen is not a normal amine. The nitrogen lone electron pair is donated to the aromatic ring system. Protonate or alkylate it and you destroy aromaticity - energetically very unfavorable....

Title: Thanks lillenthal
Post by: SPISSHAK on June 21, 2002, 10:29:00 PM

That answers my question thanks for the insight.