Author Topic: dialkyltryptamine synthesis through alkyliodides.  (Read 2905 times)

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SPISSHAK

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dialkyltryptamine synthesis through alkyliodides.
« 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...

Lilienthal

  • Guest
indole nitrogen is not an amine
« Reply #1 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....

SPISSHAK

  • Guest
Thanks lillenthal
« Reply #2 on: June 21, 2002, 10:29:00 PM »
That answers my question thanks for the insight.