The Vespiary

The Hive => Novel Discourse => Topic started by: foxy2 on April 01, 2002, 08:48:00 AM

Title: Novel route to Ephedrine and possibly its analogs
Post by: foxy2 on April 01, 2002, 08:48:00 AM
This seems like an easy way to dl-ephedrine from propenylbenzene.  I wonder if it will work on substituted propenylbenzenes?  I think it will.
The ephedrine analog of MDMA?  That could possiblly bee oxidized to the methcathinone analog of MDMA.
Interesting!!  :)

Reactions of aliphatic epoxy compounds. IV. New route for DL-ephedrine synthesis.    
Lunge, Jerzy; Belzecki, Czeslaw.    
Acta Polon. Pharm.  (1961),  18  177-81. 
Journal  written in Unavailable.   
CAN 56:60359    AN 1962:60359   

cf. CA 54, 2236f.

A practical method for DL-ephedrine (I) synthesis was outlined, cis-Propenylbenzene (23.6 g.) (from decarboxylation of trans-a-methylcinnamic acid) added to 51 g. perphthalic acid in 480 ml. CHCl3, the mixt. filtered after 24 hrs. at room temp., and the filtrate distd. gave 24 g. erythro-DL-1,2-epoxy-l-phenylpropane (II), b18 95-7°, n20D 1.5222.
II (13.4 g.) heated 10 hrs. at 100° with 6.8 g. 20% MeNH2 in MeOH yielded 12.2 g. DL-pseudoephedrine (III), m. 116-17° (ligroine).
III (20.1 g.) refluxed 25 hrs. with 100 ml. 25% HCl, the cooled soln. neutralized with 10% NaOH, treated with 6.3 g. (CO2H)2 in 25 ml. H2O, the collected ppt. treated with 50% NaOH, the amine taken up into C6H6, and the soln. satd. with dry HCl gave 8.1 g. I.HCl, m. 189-90° (PrOH).

Those who give up essential liberties for temporary safety deserve neither liberty nor safety
Title: Decarboxylation?
Post by: psychokitty on April 01, 2002, 08:06:00 PM
Does the article have a reference to that decarboxylation reaction?  Maybe some experimental details? (I'm requesting such information in another thread.)

If this works then I'm sure that reacting the epoxide with hexamine followed by acid hydrolysis would work equally well to yield norpseudoephedrine.

Another way to isomerize the pseudoephedrine into ephedrine is with 50% H2SO4 for 2 hours and 17 min at 117 C.  Reported yield is somewhere a little above 50%.
Title: sorry
Post by: foxy2 on April 01, 2002, 11:20:00 PM
Thats how I found this article, lookin for a decarboxylation ref for you  :)

I posted everything I have.  I am not even sure if the decarboxylation details are in there.  You would have to dig the article up and most likely translate it from Polish.

Those who give up essential liberties for temporary safety deserve neither liberty nor safety
Title: Dig it up
Post by: Rhodium on April 01, 2002, 11:34:00 PM
If someone fetches that article, we have polish translators at our service at the board. Polish isn't THAT hard to decipher anyway, it's about as hard as italian/french.