indigo758 (Stranger)
04-18-03 21:44
No 427883
      5-meo-dipt synthesis  Bookmark   

Now that good old foxy is schedule 1, the crew is looking for ways to obtain more. A colleague versed in MDMA synthesis offered to give it a try if we could manage to find a decent recipe. After searching for some time, I was not able to come up with a lot of info besides the TIHKAL entry. Anyone out there have any input? Now I'm not a high-grade chemist here, just collecting info for one. Can 5-meo-dipt be made from the same resources as MDMA? ANY input is much appreciated.
 
 
 
 
    Chimimanie
(Hive Bee)
04-19-03 00:35
No 427917
      synthetic approach  Bookmark   

Obtain some 5-methoxy-tryptophol, then mesylate it and swap that with diisopropyl amine in DMSO.

If your friend doesn't know how to obtain 5-methoxy-tryptophol, he should not synthetise the compound.
 
 
 
 
    fathornet
(Stranger)
04-23-03 09:20
No 428889
      best route to 5-meo-dipt  Bookmark   

chimimanie
i thought the only synth was the tikhal entry by the good doc shulgin???
i beleive he starts with 5 methoxytryptamine which i thought was the health food supplement meletonin.
do you have details or refs for your dipt synth???smile
 
 
 
 
    Lilienthal
(Moderator)
04-23-03 10:30
No 428904
      Melatonin is N-acetyl-5-methoxy-tryptamine,...  Bookmark   

Melatonin is N-acetyl-5-methoxy-tryptamine, not 5-methoxy-tryptamine.
 
 
 
 
    fathornet
04-23-03 19:15
      Clarify dipt synth, please
(Rated as: UTFSE!)
 Bookmark   
 
 
 
    fathornet
(Stranger)
04-23-03 19:34
No 428997
      5 methoxy tryptophol?  Bookmark   

chimimanie
swif wants to do the dipt synth but cant find the 5 methoxytryptophol. Only places were chem co.s on the net carrying chemical intermediates.
is this material easily available?
 
 
 
 
    Chimimanie
(Hive Bee)
04-24-03 02:51
No 429050
      Fathornet
(Rated as: excellent)
 Bookmark   

If you have access to org chem journals look those references:

in Post 427106 (Chimimanie: "On tryptophol", Tryptamine Chemistry)

244a,b for 5-MeO-tryptophol
681 for the alpha-methyl derivative as well as 739
687 and 688
and 231 and 673 for the 5-benzyloxyderivative

look those posts (As well as the threads which contain them!)
Post 218769 (foxy2: "Tryptophol Synthesis", Tryptamine Chemistry) just use 4-MeO-phenylhydrazine instead (avaiable from oversea suppliers), or the synth is at rhodium's site.
Post 407891 (Rhodium: "o-Iodoaniline + Butynol -> Tryptophol -> DMT", Tryptamine Chemistry) the mesylate swap, you could use tosylate, but maybee side reaction could occur due to solvent effects
Post 197106 (Lilienthal: "Re: looked up some nice ref's", Tryptamine Chemistry) (Yes PBr3 could bee used instead)
Post 412787 (Chimimanie: "N-Methylisopropylamine for MIPT and the like", Tryptamine Chemistry) could give you some hints.

And IMHO the best method to obtain 5-Meo-tryptophol is from the 4-MeO-phenylhydrazine and dihydrofuran (or another furan derivative like foxy described) , with a little dash of ZnCl2. This method bypass the Na/EtOH or LAH reduction, which are tedious and use suspicious chemicals.

Otherwise plenty routes are of course avaiable, the indoleglyoxyl chloride one (from  5-MeO-indole + oxalyl chloride then Diisopropylamine work as well (see Journal of Heterocyclic Chemistry  (1983),  20(4),  1031-6 for a ref on 5,6-methylenedioxy indole)) for instance, or the various fisher indole synthesis see all the thread Post 335108 (Rhodium: "Fisher Tryptamine Synthesis - is this right?", Tryptamine Chemistry).

And if you understand french, the 5-methoxy-3-indolyl-N,N-diisopropylglyoxylamine is cited and prepared in Bull. Soc. Chim. France  (1965), (5),  1411-17.

This is a part of the abstract of that text:
In an alternative method, 5-methoxyindolyl-2-carboxylic acid (IV) was decarboxylated in 73% yield by heating at 230 in a Peligot tube until evolution of gas was complete.  Alternatively, a mixt. of 70 g. IV, 150 cc. quinoline, 8 g. Cu(OAc)2, and 4 g. powd. Cu was refluxed 3 hrs. and extd. with Et2O.  The org. ext. was washed 4 times with 2N HCl, then H2O, dried, and distd. to give 72% 5-methoxyindole (V), b0.2 125-30, m. 57.  A soln. of 55 g. (COCl)2 in 60 cc. Et2O was added to a soln. (cooled to 0) of 50 g.
V in 600 cc. dry Et2O.  The mixt. was stirred 1 hr. and filtered to give 85 g. 5-methoxyindolyl-3-glyoxylyl chloride (VI).  A mixt. of 12 g. VI, 10 cc. 40% aq. Me2NH, and 200 cc. ice water was stirred 4 hrs. at 0 to give 87% 5-methoxy-3-indolyl N,N-dimethylglyoxylamine (VII, R1 = R2 = Me) (VIII), m. 221
Redn. of VIII by LiAlH4 in tetrahydrofuran as described previously gave 81% 5-methoxy-3-(2-dimethylaminoethyl)indole (IX, R1 = R2 = Me), the hydrochloride of which m. 146.  R1, R2 5-Methoxy, % yield, M. p.; Et, Et, 80.5, 160; Pr, Pr, 91, 150; iso-Pr, iso-Pr, 75.5, 225

So 5-MeO-DipT is avaiable in 75% yield from the reduction of the glyoxyl amide which is avaible from 5-MeO-indole and oxalyl chloride followed by reaction with aqueous diisoproplyamine. 5-MeO-indole is avaiable from the 5-methoxyindolyl-2-carboxylic acid which itself should be avaible from the 4-MeO-phenylhydrazine through a Japp-Klingemann reaction. Alternatively the 5-MeO-indole is avaiable also from air oxydation of beta-ethylamino-hydroquinone, see ref [8] of Post 407846 (Chimimanie: "Proposed method (1) for 2C-H", Novel Discourse) or by other means I dont know by heart.


But I prefer to do one fisher synthesis and no reduction, starting from scratch I really think the tryptophol road is the best.

UTFSE and you should also read Heterocyclic Compounds, Indoles, Part 1,2 and 3, Houlihan, Wiley

peacecool