(Chief Bee)
09-16-04 18:58
No 531710
(Rated as: excellent)
Synthesis of N-Alkyl-N-Hydroxyamphetamines and Related Nitrones
A. H. Beckett, R. T. Coutts and F. A. Ogunbona
Tetrahedron 29, 4189-4193 (1973) (../rhodium/pdf /n-oh-ampheta
Abstract
The action of m-chloroperbenzoic acid on various amphetamines and on dibenzylamine is shown to yield N-hydroxy derivatives and related nitrones.
____ ___ __ _
Synthetic Routes to Optical Isomers of Primary and Secondary Hydroxylamines of 1-Arylisopropylamines
A. H. Beckett, K. Haya, G. R. Jones and P. H. Morgan
Tetrahedron 31, 1531-1535 (1975) (../rhodium/pdf /n-oh-ampheta
Abstract
A number of optically pure primary 1-arylisopropylamines were converted to 3-phenyl-2-(1'-arylisopropyl)oxaziridine
The Hive - Clandestine Chemists Without Borders
(Hive Bee)
09-17-04 18:32
No 531888
That is an interesting article, Rhodium.
Now the few remaining RC companies could give us
N-hydroxymethamphetamine with ease, I suppose. It's not that much different than supplying methylone or 4-fluoroamphetamine, right?
(Hive Bee)
09-17-04 18:46
No 531891
Now the few remaining RC companies could give us
N-hydroxymethamphetamine with ease, I suppose. It's not that much different than supplying methylone or 4-fluoroamphetamine, right?
Not quiet. In order to make the N-OH-amphetamines following this method at least they'd have to pass the illegal ampetamines. Situation like this is also probably the major reason you haven't seen DOI pushed by them, as they need to go via illegal 2,5-DMA, alternatively another route which would upon reduction give some 2,5-DMA. But there is an easy way around that, luckily, they are blind to see it...
(Hive Bee)
09-17-04 18:48
No 531892
There is a prescription drug in the US called methoxamine (which is chemically 2,5-dimethoxyphenylproponalamine) which could be reduced ala one of the (pseudo)ephedrine to methamphetamine methods to 2,5-DMA. (I think.)
Is this what trick you are alluding to? I kind of doubt it. You have just piqued my interest, though. Do tell.
(Chief Bee)
09-18-04 09:56
No 532000
methoxamine (which is chemically 2,5-dimethoxyphenylproponalamine) which could be reduced ala one of the (pseudo)ephedrine to methamphetamine methods to 2,5-DMA. (I think.)
Nope, any HI based reductive protocol will demethylate the methoxy groups with more ease than the alcohol being reduced.
The way around 2,5-DMA is to make 4-Iodo-P2P and reductively aminate that.
(09-20-04): Edit: Naturally I meant 4-Iodo-2,5-dimethoxy-P2P. You would have to research/experiment to find a procedure which did not effect dehalogenation of the ring though, but there are several mild methods available out there.
The Hive - Clandestine Chemists Without Borders
(Hive Bee)
09-18-04 14:49
No 532040
The way around 2,5-DMA is to make 4-Iodo-P2P and reductively aminate that.
Sounds like the first thing that comes to mind, but, what about dehalogenation of the fragile iodine during reduction(s)? Even the minimal dehalogenation would render the route useless law-wise.
(Newbee)
09-19-04 16:05
No 532228
many ways to skin this particular cat, for example diazotising 4 amino DMA, itself produced by reducing 4nitro 25 dimeo alpha methyl nitrostyrene, first with LAH and then with hydrogen over palladium (or even old fashioned Sn/HCl) The aliphatic amine is unaffected by diazotisation provided the pH is controlled and kept strongly acidic the protonated amine is unaffected.
i shall now slink back off to my cave
09-19-04 17:53
(Rated as: Off-topic pseudoscientific/contrafactual rambling)
(Hive Bee)
09-20-04 01:03
No 532296
O Rhodium,
Oh yes, I do confess, I did digress, at length, at best. With pseudoscientific ramblings better suited to a diary than to this game, this game, our game of chess.
But how on Earth you plan to get 2,5-DMA or DOI from reductively aminating 4-iodo-P2P is well beyond me. I thought that the synthesis would at least involve 2 methoxyphenyl groups somewhere and at some point, no?
Captain_America,
To avoid dehalogenation such as de-iodination of the benzene ring, one must be careful to keep the temperature cold and to use only 1 equivalent of LAH. Using this method usually does not strip away the aromatic halogen.
obia, How do you plan to obtain the 4-nitro-2,5-dimethoxyphenyl-2-nitroprope
However, synthetically speaking, I find your proposed synthetic outline to be factually correct if not a tad bit too laborious, or perhaps as the case may be, just laborious enough to work as you might reply.
(Chief Bee)
09-20-04 03:24
No 532307
Excuse my typo, I have added a correction to Post 532000 (Rhodium: "Methoxamine is no good precursor.", Novel Discourse)
The Hive - Clandestine Chemists Without Borders
(Hive Bee)
09-20-04 04:06
No 532311
Even if the ephedrine-DMA route you propose worked w/ RP/HI, it wouldn't bee cool to bee ripped-off by pharmaceutical companies and extract the precursor from thier shitty tablets for this synthesis...
But, if you really like that route read: Post 504623 (Kinetic: "Another way to methaephetamine", Novel Discourse)
(Hive Bee)
09-20-04 10:54
No 532346
To avoid dehalogenation such as de-iodination of the benzene ring, one must be careful to keep the temperature cold and to use only 1 equivalent of LAH. Using this method usually does not strip away the aromatic halogen.
This would not work while the iodine is on, period. Temperature has little significance, nor does stochiometry, the hydride ion (theoretical) is a very powerful nucleophile, it would replace the iodine on the ring to some extent.