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4-Methylaminorex Synth w/o CNBr

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Rhodium:
The "4S, 5S" thing is to indicate the chirality of the carbon atoms at the 4- and 5-position on the heterocyclic ring, they don't indicate the position of the second methyl. It could be anywhere, but I find it most likely it would be on the 3-positioned nitrogen if nothing else is said. But I guess someone have to fetch that article just to be sure.

cilliersb:
This seems to be exactly what I was looking for Chief.

It looks to me like your new method will also work for NorPseudoE.HCL HaHaHaHaHa!

How come I'm seeing HOCN in the pictures and KOCN in the literature. Which one did you edit Mr. Chief Bee?

See you guys on the other side....... 8)

Rhodium:
The reaction calls for pseudoephedrine hydrochloride and KOCN, which in my reaction diagram (and the original diagram in the article) has been "translated" to HOCN and pseudoephedrine freebase. I consider the terms to be interchangeable, because the intermediate product (N-carbamyl-(±)-pseudoephedrine) is essentially an addition of HOCN to pseudoephedrine if you count the atoms. The Cl- from the hydrochloride and the K+ from the potassium cyanate are only spectator ions in the reaction.

To my knowledge, free HOCN cannot be made as a stable solution, that's why it is generated in situ.

cilliersb:
Thanks for that little clarification Chief!

I still say that logically d-NorPseudoEphedrine will work and the beauty of it is that you then, according to your refs above, would end up with the trans isomer of 4-MAR.
4-DMAR would be produced with PseudoEphedrine.

Nor, Nor, Nor. it's the Nor that makes the difference boys.

Let the flames begin!  ;)

Rhodium:
I would welcome any reports of using norpseudoephedrine (phenylpropanolamine) in the potassium cyanate reaction, either in this thread or in email.

Now when we know that the reaction proceeds through an urea derivative, what other methods are at our disposal to form it? Reaction of urea with a styrene halohydrin?

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