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CuReUS
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No it wasn't
Quote: Originally posted by tsathoggua1  | Went wlth doing the alkylation first. Will report on the results once the acylation is complete.
That, on the other hand, I am looking forward to much less, considering its butyric anhydride. Never handled the acid, but have heard nothing pleasant
about the odour.
Just awaiting the fixing of my stirplate, which couldn't have picked a more annoying time to stop working. Should be done today though.
Ended up refluxing the alkyl halide with a very little light naphtha, using of all things, a hairdrier on maximum output, since a friend of mine
kindly donated one that can, at least if pointed at human flesh, only be described as vicious. If all, despite the setback, went well, and the product
was alkylated as desired, I think I'll try acylation of just 1/4 of the product (done on a 4g scale, since the piperazine mono-phosphate came
conveniently in 4g packages as de-worming medicine. Even that should be sufficient to verify activity.
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tsathoggua1
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My bad, memory fails me. Thanks for pointing that out. I certainly tried it both ways round however. Yield was relatively low of what is believed to
be the acylated product, being that 1-formylpiperazine is reported to be a golden or amber oil, that is pretty much accurate as to one of the two
products from running it acylation-first. Most was a product that was determinedly insoluble in pretty much everything thrown at it (xylene, acetone,
iPA, solubility test in methylated spirits although this was solely to test for potential extraction methods on a small quantity. Diethyl ether,
diisopropyl ether, pentane, heptane, xylene/acetone/heptane/DIPE/EtOEt mixture, light naphtha, mineral spirits. Didn't have any DCM at the time, and
was still making a batch of CHCl3, that, acetonitrile, GAA and EtOAc were the only things not tried.
Acylation with propionyl chloride in acetone produced a very thick, amber colored syrup-like substance, I've since read that it can be done in high
yields (I intend to go via N-propionylpiperazine, alkylate and then decarboxylate and reacylate using n-butyric anhydride. This is because the
propionylpiperazine derivative apparently shows some opioidergic activity (the alkylated N-cinnamyl-N-propionyl homolog) but texts differ as to
greater or lesser activity than the 4-carbon species, and N-propionylpiperazine also has direct value to me for its use as ideal precursor for DM-235,
N-propionyl-4-benzoylpiperazine, one of the AMPAkines, positive allosteric modulators of AMPA-sensitive ionotropic glutamate receptors that facilitate
LTP, learning, memory and wakefulness, but which lack the excitotoxic properties of orthosteric AMPAr agonists such as domoic acid (a marine biotoxin
produced by dinoflagellate organisms, responsible for amnestic-type neurotoxic shellfish poisoning after shellfish feed on such planktonic blooms and
bioconcentrate domoic acid within their tissues. Don't know if it does them any harm, but I doubt your average clam, mussel, oyster etc. has much of a
brain to begin with), which do quite the opposite, causing a massive influx of calcium to the intracellular space and cause severe and quite likely
permanent destruction of those same cognitive resources, directly killing cells, and targeting the hippocampus especially.
Need to get more piperazine for another shot. Got enough left for attempt on the scale of a couple of grams but thats about all I have left
(piperazinium hydrogen phosphate)
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CuReUS
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You will have to hydrolyse the N-propionylpiperazine after you alkylate it,you can't decarboxylate an amide.You could try the references I suggested
on pg 1 before you go about this convoluted route
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