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SuperOxide
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I chat with Benignum outside of SM, so I've had some previews of this as he's shared some pictures and info on his progress. But I had no idea it was
_this_ epic (literally, epic).
Benignum, thanks for sharing such amazing work. Definitely an inspiration! 
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Benignium
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Thank you, both of you! I appreciate your positive feedback like you wouldn't believe.
timescale - This is a good question that I'm afraid I don't have a good answer to. The suspicion is very non-specifically based on
reports I've read online as well as my own experiences working with these compounds and is, for all intents and purposes, just a hunch. Indeed, the
moisture present in DCM, albeit very minor, could play some part in such a phenomenon, much like the impurities accompanying crude substances
themselves are sometimes seen doing.
The thiophenols definitely seem like an attractive angle of approach in the preparation of the 2C-T-x compounds, but currently I'm undecided on the
specifics.
As for the bioassays, I could consider posting thoughts on my subjective experiences here on this thread, though I would prefer to have the
moderators' explicit blessing first. What's more, finding the time for those subjective experiences has proved somewhat challenging so far. Do let me
know any specific questions you might have, however!
[Edited on 18-4-2022 by Benignium]
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xdragon
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Great content as always, Benignium.
I don't know if you remember, but I talked to you earlier outside of SM when I found you "in the wild" about stereo-selectivity
issues/overchlorination of 2C-H which may form 4,6-dichloro-2,5-dimethoxyphenethylamine and was reported in the literature, which lead to some groups
adopting to different synthetic schemes: chlorination and purification of the starting aldehyde and choosing a reduction which does not dehalogenate,
starting from 2C-B, etc.
It would be nice if we knew how much of a problem this overchlorination is with NCS and N-chlorosaccharin. At the other place - the vespiary - a user
lately reported NCS chlorination of 2C-H and had multiple spots both on TLC as well as an instrumental chromatogram (too tired to log back in, but see
for yourself). Sadly, no qualitative analysis of the peaks could be done.
If you see any way of getting qualitative analysis of both your crude and purified 2C-C and DOC done, that would be very interesting to the whole
community and some nice chemistry work.
All the best to your continued efforts at phenethylamine chemistry - or just chemistry in general, we don't always get to be picky 
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Snakeforhire
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@Begnigium :
You sir, deserve the highest praise for such a comprehensive report, and I extend my deepest thanks to you for this tremendous effort. 
[Edited on 10-6-2022 by Snakeforhire]
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Snakeforhire
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I'm new here and have just learned of nitroalkenes reduction with NaBH4 and a metal salt so y'all have to forgive my ignorant ass if this has been
covered already (not in any post that I could find yet though), but I need some experts' advice :
Is there a significant yield difference between such a reduction done with Ni(II) and Cu(II) salts ?
I'm only asking because I might know where to get some 2,5-DMB, but NiCl2 dihydrate salts are kinda hard to find : all I can find is the hexahydrate,
which I'd have to dehydrate myself and this is a major PitA...
It'd be way easier to find copper chloride actually.
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clearly_not_atara
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I think you probably want to reread the report because this reduction was carried out with copper catalyst and nickel is not mentioned anywhere.
[Edited on 04-20-1969 by clearly_not_atara]
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Snakeforhire
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I know, but I've seen in other threads that other people use nickel salts also.
I just wondered if the metal salt used can make a noticeable difference in the yield of amine.
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karlos³
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Yes it does, with a Ni(II) salt, you probably won't get any yield out.
So far, anecdotal reports of a successful NaBH4/NiCl2 reduction of a nitroalkene are very scarce.
And anecdotal reports from people who failed with it are plenty.
With Cu(II) salt, it will be easy and probably will work on the first try.
And so far, actually everyone has got it to work.
I would call that a "noticeable difference in yield"
verrückt und wissenschaftlich
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lithiumion656
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Is there any known way to induce ring closure of phenethylamine to form indole? I know the chemistry doesn't make this likely but that doesn't
discount some obscure paper/person having found a way to do so.
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myr
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Quote: Originally posted by lithiumion656  | | Is there any known way to induce ring closure of phenethylamine to form indole? I know the chemistry doesn't make this likely but that doesn't
discount some obscure paper/person having found a way to do so. |
Not practically: looking at the synthons, the disconnection between the phenyl ring and the nitrogen would need some sort of Pd or Cu coupling between
an aryl-halide, boronic acid etc. and the N, or SnAr (which would first need substantial modification of the aromatic ring)
If you want to go from a phenethylamine-like backbone to an indole, the best way (I think) would be a 2-nitroaryl nitrostyrene intermediate: acid and
a reducing metal (Zn? Sn? Fe?) would give you an indole with OK yield, probably. I believe this is even used by Shulgin for one of the stranger
indolic psychotomimetics, so it should be robust chemistry.
[Edited on 17-6-2022 by myr]
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Snakeforhire
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| Quote: Originally posted by mr_bovinejony | | Dissolve 2ch in a minimum amount of gaa and add an equal weight of nbs! The product will precipitate after some time of stirring. But the 2ch has to
be pretty pure, I've done it a few times myself |
Forgive me for bumping up your (kinda) old post -and for cluttering Begninium's thread - but you wouldn't happen to have noted the yield you got from the NBS bromination, have you ?
I'm very curious as to what the difference between reactions done elemental bromine in GAA and NBS. I can't seem to find any definitive answer
anywhere, not for lack of trying though. 
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clearly_not_atara
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| Quote: Originally posted by lithiumion656 | | Is there any known way to induce ring closure of phenethylamine to form indole? I know the chemistry doesn't make this likely but that doesn't
discount some obscure paper/person having found a way to do so. |
You can, but you can only form 5,6-dihydroxyindole, and the reaction is spontaneous by cyclization of 4-aminoethyl-o-benzoquinone. This is the
preparation of e.g. adrenochrome (which, despite repute, is inactive).
[Edited on 04-20-1969 by clearly_not_atara]
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