Name that amine?

[bell]

Could someone help with this amine, What I amine is, (haha) its a secondary amine, but which one?             
                                                       
       CH3                                              
       !                                             
      HC-COOH                                        
       !                                             
      HN-CH3
I sure hope that lets you know the amine I wanted named.

Thanks

[GC_MS]

I think it is N-methyl alanine. It's an amino acid derivative.
-[ A Friend With W33D Is A Friend Indeed ]-

[Aurelius]

Hey GC_MS, you're correct. N-methyl alanine.  good luck getting it without some synthesis on your part or some heavy fees for custom synthesis.  small molecule, not hard to make, but aurelius hasn't seen many around who supply it.

[bell]

In a Merke I have it says Formation of alkamines by heating mixtures of aromatic aldehydes and amino acid. If the amino group is secondary then the following reaction takes place, then it show benzaldehyde + that compound = ephedrine. Unless Im mistaken on the ending product

[Aurelius]

The reaction that the book is referring to would be the Akabori-Momotani reaction.  it is used for the formation of serine derivatives.  yes, you've figured out the method for ephedrine.  if you'd like here's some more specific information regarding what you're looking for.

Patent US04501919

Patent DE839500

Patent DE1086242

Patent DE960922

Patent DE1140198

Patent FR1017396

those are all patents regarding such reaction


Akabori S., Momotani K., J. Chem. Soc. Japan, 1943, 64, 608; C. A., 1947, 41, 3774
Dose K., Ber., 1957, 90, 1251.
Belikov V. M., Izv. AN SSSR. OHN, 1969, 2536

http://www.pmf.ukim.edu.mk/PMF/Chemistry/reactions/akabori2.htm

start there for details on how to do everything.  the first german patent will probably be the most helpful. 

have fun!!!

[blondie]

Aurelius thanks for finding and posting those patents. there are 3 distinct routes to meth via ppa which would mean that your not locked into one mechanism if the alanine, benzaldehyde condensation does work to yield ppa.

ppa + formaldehyde --> oxazoladine (reduce) --> meth
ppa (reduce) --> amphet + formaldehyde --> imine (reduce) --> meth
ppa + H2SO4 (steam distill)~60% --> p2p --> meth