Possible for norephedrine --> --> 4-MAR w KOCN?

[bottleneck]

I have just received the article originally cited by Rhodium in "4-Methylsminorex wo BrCN", and it seems (+/-)-ephedrine gives an imino-analogue of the 3,4-dimethylaminorex, (+/-)-trans-2-imino-3,4-dimethyl-5-phenyloxazolidine, when N-carbamylated and acid hydrolyzed.

Wouldn't (+/-)-norephedrine react in a similar way to give the imino-analogue of 4-MAR, (+/-)-trans-2-imino-4-methyl-5-phenyloxazoline?

And wouldn't the imino-group reducible to an amino-group, to result in 4-MAR?

How would one reduce the imino-group?

[bottleneck]

I read in an old chem book that imines like R-CH=NR can be reduced to amines by NaBH4.

Do you guys think it would work the same on the imine in question to give the amine?

[SPISSHAK]

will saturate the 2 imino position of the intermediate.
just go ahead and do it, it will work.

[dennis_pro]

Rhodium's paper is quite interesting and I have some questions too:
1. Is aminorex (without 4-methyl group) active?
2. What about activity of 2-amino-5-(2,5-dimethoxy-4-bromphenyl)-2-oxazoline?
3. Can be 2-amino-5-(2,5-dimethoxy-4-bromphenyl)-2-oxazoline produced from MIDODRINE after hydrolysis w/KCNO, similarly of producing 4-MAR from PPA?
4. What about producing 2-amino-4-methyl-5-(2,5-dimethoxy-4-bromphenyl)-2-oxazoline from methoxamine? Is it optically correct isomer?
With best regards,
Dennis Prochko aka Wolf

[PrimoPyro]

1.Yes, this substance is called Aminorex, and is active, but the effects are mixed, some like it, most do not. Is is also very unhealthy, causing heart problems.

2.Unknown bioactivity as far as I know, but Lilienthal said long ago that he suspected it would be "interesting" as most methoxylated subtitutes on phenethylamines are.

3.Mexamine is an entirely different compound totally unrelated to these structures. I don't see how one could produce an oxazoline from a tryptamine.

https://www.thevespiary.org/rhodium/Rhodium/chemistry/mexamine.html

As for midodrine, yes, you could use it to produce the 4-desmethyl aminorex analog, and as far as I know, this compound is untested as well. It has never been reported HERE at least.

PrimoPyro
Will perform sexual favors for females in exchange for 1,2-dimethylaziridine. PM for details.

[dennis_pro]

MEXAMINE is a 5-MeO-tryptamine, correct.
I mean Methoxamine, not a MEXAMINE, sorry. I'll correct my message.
What about Methoxamine?
With best regards,
Dennis Prochko aka Wolf

[PrimoPyro]

I still don't see how you would make that compound you want from Methoxamine, which Chemfinder.com says looks like this:



It has none of the methoxy substitutes you want, and it is still a tryptamine. To get the compound you want from this chemical, you have to add the methoxies, and cut out the entire middle of the molecule. It technically could be possible, but I haven't the slightest clue where you would start.

[EDIT]It's not a tryptamine, it has one too many carbons. It's an indole-propanamine.[/EDIT]

PrimoPyro
Will perform sexual favors for females in exchange for 1,2-dimethylaziridine. PM for details.

[dennis_pro]

Methoxamine (Vasoxine)is a 2,5-dimethoxy-PPA. But I don't know it optical configuration and this is a problem.

See

https://www.thevespiary.org/rhodium/Rhodium/chemistry/yadontsay/

With best regards,
Dennis Prochko aka Wolf