Bandil
(Hive Bee) 04-27-02 23:01 No 302204 |
DPT synth via propyliodide and ethanolamine | Bookmark | ||||||
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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hypo (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. |
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Bandil (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? Thanks |
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hypo (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. |
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Rhodium (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. |
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UTFSE (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!!!! |
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Rhodium (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. |
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Lilienthal (Moderator) 04-29-02 02:58 No 302779 |
methylations only | Bookmark | ||||||
The ethanolamine route does work only for methylations if I remember correctly. |
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