The Vespiary
The Hive => Tryptamine Chemistry => Topic started by: Bandil on April 27, 2002, 11:01:00 PM
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Hi!
Swim was pondering the synth of DPT, using tryptamine and propyliodide. Shulgin uses some quite exotic catalyst for this reaction. Can anyone explain what it actually does?
I also read about people using ethanolamine instead of the catalyst. Is this feasible for the DPT synth?
The full synth swim was thinking about was:
Tryptamine + propyliodide -> quad-PT
quad-PT + ehtanolamine -> DPT
What about yeilds, how are they? Would it be possible to do the reaction in one shot, by simply mixing all of the reagents?
Thanks!
Regards
Peter
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i'm pretty sure that you are wrong.
quaternization seems not to be a problem with DPT (or anything higher than methyl). but you need a base to catch the HI or HBr formed in the reaction.
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OK, so you are suggesting that swim could do it with tryptamine + propyliodide + [Some Base] -> DPT? What bare would you suggest? Ammonia, triethylamine or what?
Thanks
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well, i would suggest diisopropylethylamine, but only because shulgin uses it in tihkal, not because i understand this chemistry stuff.
ammonia is obviously bad, because you don't want to alkylate your base, do you? i guess the more sterically hindered, the better.
there's also some stuff in tfse about using PTC/NaOH.
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Any sterically hindered tertiary amine should work, triethylamine and trimethylamine would probably just be alkylated. Hünig's base (diisopropylethylamine) is perfect - it is not nucleophilic at all.
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how does one make ethanolamine (sounds like ethyl and a amine) ?
I haven't found a straight forward synth from looking around.
this is a pre to morpholine.
OTEECEE & meeeee!!!!
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Addition of ethylene oxide (oxirane) to ammonia. But ethanolamine is so cheap it is unnecessary to make it yourself.
A ghetto variety would be to react ethylene glycol with HCl to get 2-chloroethanol, which is then reacted with ammonia to give a mixture of mono-, di- and tri-ethanolamine.
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The ethanolamine route does work only for methylations if I remember correctly.