Bandil (Hive Bee)
04-27-02 23:01
No 302204
      DPT synth via propyliodide and ethanolamine  Bookmark   


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?

(Hive Addict)
04-27-02 23:08
No 302207
      wrong  Bookmark   

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.
(Hive Bee)
04-27-02 23:49
No 302222
      what base then  Bookmark   

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?

(Hive Addict)
04-28-02 00:02
No 302235
      i suggest dipea  Bookmark   

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.
(Chief Bee)
04-28-02 16:19
No 302559
      base  Bookmark   

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.
(Hive Bee)
04-29-02 00:44
No 302734
      a little of the subject  Bookmark   

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!!!!
(Chief Bee)
04-29-02 02:48
No 302776
      Ethanolamine synthesis  Bookmark   

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.
04-29-02 02:58
No 302779
      methylations only  Bookmark   

The ethanolamine route does work only for methylations if I remember correctly.