In place of the traditional halide or nitro at the 7 position, this compound has an ethynyl group. It was developed to find a benzo that more closely
mimiced the effects of alcohol. I wonder about the addition of a '2 flouro group to increase potency. Now, the starting benzophenone is not available
and reading the Chinese papers I see that they started from diazepam. I am interested to know of the most simple route to make this compound.
Obviously, starting from diazepam LOOKS the simplest, but the paper uses some very wacky route. Would forming the sodium salt of ethylene allow
addition?solo - 8-11-2008 at 08:13
.......piglet it would help if you provided a pic of the compound in question,....also welcome to the forum,... bee ........solo/javaUnintentionalChaos - 8-11-2008 at 23:00
If they went a very complicated route to get the final product, there is a good reason to do so. If your goal is to swap the chlorine on diazepam with
an ethynyl group as in the attached image, you cannot do it by simple substitution with acetylene.
While it is true that you can deprotonate acetylene or terminal ethynyl derivatives (forming a carbanion, a powerful nucleophile) with sodium amide in
an appropriate solvent (liquid ammonia perhaps), the SN2 reaction will not occur with aryl halides like diazepam. If it were an alkyl halide, the
reaction would occur, but the only way to do a "backside attack" on the *planar* benzene ring would require the ethynyl carbanion coming through the
ring itself, which flat out will not happen. The other possible mechanism is for the SN1 mechanism to take over, but dissociation of the chlorine
would form a benzene cation, which is extremely disfavored and will not happen readily enough for the reaction to proceed.
[Edited on 11-9-08 by UnintentionalChaos]
vulture - 9-11-2008 at 08:18
Sonogashira would be an option if you had a bromine, or even better, iodine, instead of a chlorine there. That said, maybe Sonogashira works with
activated chlorines. Literature searching will be in order to answer that question.smuv - 9-11-2008 at 12:23
You would need TMS-acetylene though for the sonogashira lest you want a polymer...chemrox - 9-11-2008 at 18:27
Have you searched ACS, JCS, etc.? The more accessible journals? Is there a patent that cites papers one could get more info from?Nicodem - 10-11-2008 at 01:07
Questions without providing the necessary references that describe what is being discussed are to be addressed in the Beginnings section.
(I'm moving this thread there)Piglet - 14-11-2008 at 06:52
I am interested in two distinct aspects of this LEGAL compound. Firstly, I am interested in the synthesis from diazepam. The original patent uses a
route I have not see before (pardon my ignorance) and secondly, this is something biochemical in nature, is how it expresses itself to produce many
effects like alcohol. A Dr. Nutt has, for some time, been advocating the use of benzos as a replacement to alcohol because of the much lower levels of
damage on the body and the fact that antagonists will terminate the effects, but not the user.
I say it's legal. In the UK it's not mentioned and the benzodiazepine class is not mentioned as a group. Benzos are class C.
I should had made it clear that in the UK, at least, it would only fall under the auspaces of the Medicines Act.
If someone is not interested then fine, but posting insults seems a pretty negative way to proceed.stoichiometric_steve - 14-11-2008 at 08:02
Quote:
Originally posted by Piglet
A Dr. Nutt has, for some time, been advocating the use of benzos as a replacement to alcohol
Did you know that you do not HAVE to take drugs to relax?
Did you also know that benzodiazepines have quite nasty long term effects, such as tachyphylaxia and withdrawal problems?
