06-21-02 08:18
No 323583
      dialkyltryptamine synthesis through alkyliodides.  Bookmark   

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...
06-21-02 16:09
No 323648
      indole nitrogen is not an amine  Bookmark   

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....
(Hive Bee)
06-21-02 22:29
No 323744
      Thanks lillenthal  Bookmark   

That answers my question thanks for the insight.