Sciencemadness Discussion Board

Fluorenone reduction

ZetekitoxinAB - 3-8-2019 at 10:16

Hi ! I have found a cheap supply of fluorenone and would like to reduce it to fluorenol (hydrafinil). I wonder if I could to this with quantitative yield using more common reagents, such as Al powder with dilute HCl or dilute NaOH.

Of course NaBH4 would work flawlessly but it is just to expensive. I could also buy Zn or magnalium (Zn-Mg) powder; would these work better? Thanks for any insights!

[Edited on 3-8-2019 by ZetekitoxinAB]

AvBaeyer - 3-8-2019 at 18:31

FYI,

Magnalium is 5% magnesium and 95% aluminum. See google.

AvB

Assured Fish - 3-8-2019 at 21:12

You could opt for aluminium amalgam as your reducing agent, ive read of some people achieving 80% yields with this.
I doubt you would get quantitative without using either H2 + catalyst or a hydride.

CuReUS - 3-8-2019 at 21:50

you could get quantitative yields by refluxing it with dithionite

Sigmatropic - 4-8-2019 at 04:21

I'm quite surprised by amount of times a mistake is copied when you search for hydrafinil. Shouldn't hydrafinil be the cyclized modafinil and not fluorenol?

I don't really see how fluorenol or benzhydrol for that matter will have any activity... Or why selling it as some sort of supplement is going to help anyone on their NZT-48 quest.

Also I think there was a thread like this on SM on how to proquire benzhydrol and the answer was something like benzophenone with zinc dust in acidic medium. But not full gas clemmensen reduction.

Update: it was zinc in ethanol with sodium hydroxide
http://www.orgsyn.org/demo.aspx?prep=cv1p0090
As in this thread, which is not so relevant to this but ah well
http://www.sciencemadness.org/talk/viewthread.php?tid=132397

[Edited on 4-8-2019 by Sigmatropic]

Metacelsus - 4-8-2019 at 05:56

Here's the relevant paper about fluorenol having modafinil-like effects:
Quote:
the wake promotion activity of the analog was likely due to an active metabolite (compound 3)


Compound 3 in the paper is fluorenol.

I don't know if there have been subsequent studies on this, but it seems interesting. I would be worried about possible toxicity since it doesn't seem like that's been evaluated yet.

Attachment: 1-s2.0-S0960894X12004702-main.pdf (265kB)
This file has been downloaded 307 times

ZetekitoxinAB - 4-8-2019 at 08:06

Thanks ! The proposed reduction methods are very nice; I would try to avoid Al amalgam if I decide to buy the fluorenone though. Ditionite reduction seems the cleanest but I will try Zn+NaOH first as they are easier to get here where I live.

Fluorenol is just way overpriced on nootropic sites; it seems to be active in doses as low as 0,1 g in humans, has a shorter duration of action and it is less euphoric than modafinil according to anecdotal reports.

Thanks for the reference Metacelsus; toxicity would definitely be an issue especially if taken long term and regularly. Still somewhat obscure compound. I doubt benzhydrol would have eugeroic properties; I believe the restricted spatial structure of the phenyl rings would be very relevant for this activity. Often you find compounds with similar pharmacology although quite distant structurally; Salvinorin A comes into my mind; it doesnt resemble any other nitrogenous k opioid agonist, for example

[Edited on 4-8-2019 by ZetekitoxinAB]

[Edited on 4-8-2019 by ZetekitoxinAB]

DavidJR - 4-8-2019 at 15:39

I don't think sodium borohydride is particularly expensive - sure, it's pricey per-gram, but if you use the right conditions you can use all 4 hydrogens and so a little goes a long way