psycosmo (Newbee)
09-08-01 00:03
No 211188
      halogenating alkyltryptamines  Bookmark   

If one were to treat an NN, dialkylated tryptamine with say Cl2, I2, or Br2, what position(s) on the aromatic ring would the halogen end up on? How does the fact that the pyrrole is attached to 2 positions on the benzene effect ortho-para substitution?
Anyway, is there any chance that the halogen might end up in the 4- position?
I note that in descriptions of the psilocin biosynth pathway the OH as added after N-alkylation
If this is so then It might be interesting to treat some plant xTracts with a halogen, then NaOH....
(Chief Bee)
09-08-01 14:17
No 211353
      Re: halogenating alkyltryptamines  Bookmark   

I don't know for sure, but I'm afraid that regular halogenation would place the halogen in the 2-position on the indole ring. But besides that, the 5-position is the most activated spot on the benzene part of the molecule.
09-08-01 15:06
No 211356
      Re: halogenating alkyltryptamines  Bookmark   

Is this a topic for the Newbee forum?


Actually officer, if you factor in the earth's rotation, we were all speeding.
09-09-01 20:37
No 211622
      Re: halogenating alkyltryptamines  Bookmark   

It's the 2-position which will be substituted.
09-28-01 07:05
No 218037
      Re: halogenating alkyltryptamines  Bookmark   

If you halogenate using Br2, you will get a mixture of 5- and 7- halogenation. The nitrogen in the 1-position activates the benzene ring, i.e. ortho-,para-directing, respective to itself. You can select the 5-position by acetylating the 1-position, which provides steric hindrance to protect the 7-position. Alternatively, you can halogenate exculsively the 7-position by selecting a halogenating agent that coordinates with the amine (the reagent escapes me at the moment.)

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