Demethoxylating PCP derivatives

Discussion in 'Synthetic Drugs' started by AceK, Feb 9, 2014.

  1. AceK

    AceK Scientia Potentia Est

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    So I was wondering if anyone here has chemical knowledge about removing the methoxy group from either 3-meo or 4-meo-PCP. If this were reasonable, it would seem like a decent work up vs the traditional PCP synth which requires some sketchy chems. What would be required, besides methoxylated PCP as a precursor of course?

    I posted this in the drug chemistry forum but feel like it doesn't get enough views. If nobody wants to say anything, that's cool and I understand. You can also PM me :)
     
  2. Hedgeclipper

    Hedgeclipper Qiluprneeels Nixw

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    I doubt any of us could do this or would know how... but as far as I know (and I don't know about more complicated aromatic compounds like pcp) you would have to use an acid to protonate O of the methoxy group, so that it would be like an OH leaving group, which you could pop off of the main molecule by substituting it with a powerful nucleophile (something like Sodium methanethiolate for example) and then eliminating the nucleophile

    how any of that would practically work I have no idea, but I think that is the basic idea of removing something like a methoxy group.

    If anyone who knows more than me would chime in I'd be interested in discussing the theory of doing something like that... although I doubt any of us are gonna do any crazy chemistry with research chemicals... :rolleyes:
     
  3. Hedgeclipper

    Hedgeclipper Qiluprneeels Nixw

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    yo! Here's a better idea:

    Maybe the methoxy in the methoxybenzene substituent of 3-MeO-PCP could be hydrolized to result in 3-HO-PCP, and then somehow that could be reduced to PCP?

    I know phenol can be reduced to benzene with zinc, for example.

    but like I don't think chemicals actually work like that. I'm not a chemist. I think that targeting just that specific methoxy group would be very difficult. IT might be easier to just synthesize straight PCP.


    The point is; I don't think it would be easy. And definitely beyond the scope of my knowledge of chemistry, but I was down to think about it...
     
  4. AceK

    AceK Scientia Potentia Est

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    Well thank you for sharing your knowledge:). Chemistry fascinates me, molecules and chemical bonds...I have much reading to do on the subject of organic chemistry.
     
  5. Hedgeclipper

    Hedgeclipper Qiluprneeels Nixw

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    Yo so I thought about it some more, and I think that I was sort of right.


    The general idea would be to protonate the oxygen on the methoxy group with a strong acid and then you could maybe reduce it with Lithium Aluminium Hydride (LiAH4)
     
  6. AceK

    AceK Scientia Potentia Est

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    Reflux with hydrioiodic acid maybe..l
     
  7. porkstock41

    porkstock41 Every time across from me...not there!

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    i would be down to think about this too (chemical reactions in general, NOT making drugs), but it's been way too long since i thought about straight up chemistry like this. i'm afraid that i have lost a great deal of knowledge...or that i never had it to begin with.

    i am becoming more and more of an expert in one particular field, and stagnating in pretty much every other field :/
     
  8. Hedgeclipper

    Hedgeclipper Qiluprneeels Nixw

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    dude that is what really worries me about academic science.

    I don't understand why it has to be structured that way. It seems like more nd more today, our society values particular knowledge over the general -- which is a good thing in some respects -- but it's als a very Brave New World "fordian" assembly line mentality. Instead of getting everyone to solve complicated multidisciplinary problems, we're all supposed to perfect one discipline an collaborate... but the collaboration is a bit of an intellectual bottleneck I would say. I don't think that the assembly line mentality should really be applied to science.

    Not that I wouldn't want to be an expert in biochemistry... Just that I think university programs should be a lot more open -- but I guess it would be hard to do everything.

    ....anyways I don't know if the reaction i suggested would necessarily work, but it would definitely be the most efficient method of reducing the methoxybenzene substituent on its own, and I don't really see why it wouldn't work on the full molecule.

    It has been interesting thinking about this. Definitely a problem beyond the scope of anything I actually need to know.

    theoretically that might work. Possibly with additional iodide salt to finish it off. Then you could do the LAH reduction. Of course in reality that shit is dangerous as fuck and I wouldn't mess with it unless I was in a nice lab... and at that point I would just make the PCP right.
     
  9. porkstock41

    porkstock41 Every time across from me...not there!

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    yeah i feel like i have read about this type of academic stagnation in dystopian sci-fi books before...

    i don't exactly know how to remedy it. i mean...it's not reasonable to be an expert in biochemistry AND chemical synthesis and physics and anthropology, etc.

    my current knowledge is very specific. but it's able to be put to use to answer a wide variety of different questions. and i could always pay better attention when i go to talks that aren't on my topic, could read more papers...but i tend to get a little bogged down in my own research (and my personal life and hipforusm ahah) to do all that.

    this link says it:
    http://matt.might.net/articles/phd-school-in-pictures/
    by MATT MIGHT
     
  10. AceK

    AceK Scientia Potentia Est

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    But isn't just making the PCP "right" also "dangerous as fuck"?
     

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