e.cryptine
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Phenylpiperazine Formation From Aniline
I'm in the process of synthesizing a phenyl-piperazine derivative (4-methallyloxy-3,5-dimethoxy aniline as the starting material) and some things have
come up that are out of my control, so I am unable to obtain bis(2-chloroethyl)amine, which I had planned on using for the piperazine ring formation.
Is there an alternative to bis(2-chloroethyl)amine for forming the piperazine ring? I do not have the resources, let alone the safety equipment needed
to work with it's intermediates (Nitrogen Mustards) to synthesize it.
I was thinking a sandmeyer rxn using KI to replace the amine with an iodine would work and then the phenylpiperazine ring would be formed using
piperazine.
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e.cryptine
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Edit:
The aniline would be nitrated with HNO3 and then the sandmeyer rxn with KI would be performed. After this the piperazine ring would be able to
displace the iodine, once the two rings are fused the nitro would be reduced to the amine using Fe/HCl and another sandmeyer rxn would be performed
using H2PO3 to eliminate the amine. I know it's not terribly efficient but any other ideas would be greatly appreciated.
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Metacelsus
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I suggest you read this:
http://www.organic-chemistry.org/synthesis/C1N/amines/arylam...
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Alice
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I'm just spoon feeding you because I don't want you to further think about working with chemical weapons. Anyhow, the compound, bis(chloroethyl)amine,
you are thinking about will polymerize anyway. But uninformed attempts making it may lead to the real mustard gas.
It doesn't happen to be a controlled substance, right?
See: https://en.wikipedia.org/wiki/2,5-Diketopiperazine#Reduction
and: http://www.organic-chemistry.org/abstracts/literature/023.sh...
Good luck with the methallyl group!
In general I think you should learn a whole lot more about organic chemistry before messing around like this. For example, why do you think it might
be a good idea nitrating the arene, reducing it, making a diazonium salt, and removing it again? 
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Dennis A
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I dont want to start a new thread but i need help narrowing down the possible ingredients in a 44% solution of piperazine wormer apart from water what
else can one expect to make extraction problematic ?
I have here,d alot of extractions on the salts but not solutions
Bear in mind i have never worked with piperazines and i am very unfamiliar with their properties so i apologize if i ask some things that are very
obvious to others
The item description gives no information apart from its concentration ,However i presume the product is more than likely a hydrochloride or citrate
salt dissolved in solution < this being water ?
Is piperazine freebase a oil ? and if so how stable is it ?
Could one freebase the solution to what PH ? 11 or 12 ? Extract with solvent wash / dry etc . Then simply re-salt it back out with HCL(aq) and
concentrate the extract crash it out with a cold appropriate solvent ?
Thanks in advance
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Dennis A
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Nothing ?
Oh well regarding the formation of phenylpiperazines with bis(2-chloroethyl)amine this is mustard gas no ? Yeah always fun when the organic reaction
you planned to perform requires the preparation of chemical warfare agents in your own home first NOT i strongly advise anyone to avoid such methods
unless your highly trained and have the correct equipment breathing equipment etc no joke
I once read a article depicting the same reaction with bis(2-chloromethylethyl)amine is this a more stable/safe intermediate for these reactions ? or
the same and yet another episode of misrepresentation of nomenclature?
Somebody please elaborate further below is a interesting read and shows many pathways the phenylpiperazines
https://www.google.com.au/url?sa=t&rct=j&q=&esrc...
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Dr.Bob
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Most commercial aryl piperazines are made via Ullman or Buchwald chemistry now. Those are the simplest ways to make them.
bis(2-chloromethylethyl)amine does not make sense, likely a typo. I have once tried to do chemistry with bis(2-chloroethyl)amine, in a proper hood,
with proper glassware, and it was a mess. There are better ways to make piperazines. I always try to run aryl reactions with mono-Boc-piperazine,
as then aryl amine is not very basic and the Boc protects the other half of the piperazine, so it becomes much less water soluble, able to be purified
via flask chromatography, and then can be deprotected to the amine HCl salt at the end to isolate them and keep them stable, as most amines oxidize
rapidly and form carbonates and other crud.
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