dormouse (Member)
04-20-00 20:00
No 108350
      Oxycodone - the easy way! -Lone Ranger  Bookmark   


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Author  Topic:   Oxycodone - the easy way! 
Lone Ranger
unregistered   posted 05-24-98 09:24 AM           
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After looking over Rhodium's site for the 100th time, and sending him numerous complaints about small details on some of the posted methods, I would like to publicly aknowlege that his is far and away the best site of it's kind, and the best maintained.
And so I offer this much requested synthesis:

HYDROXYCODEINONE: The same product obtained from the 30% hydrogen peroxide treatment of thebaine in acetic acid can also be obtained directly from codeine.

30grams of codeine in 80ml water with 25grams acetic acid, is treated cold with a solution of 20grams sodium dichromate in 25ml water. An oily precipitate forms which becomes crystal after short warming. The mixture is heated to 80deg with stirring until all the solid goes into solution; the temperature rises spontateously to 90deg. After short standing, the base is precipitated from the cold solution as the dichromate by adding an excess of chromic acid solution. Crystallize from alcohol with a little chloroform as plates, decomposes at 275deg. Stable to strong acid or alkali. Soluble in chloroform, ethyl acetate, ligroin. Sparingly in alcohol, insoluble in ether or water.

Simple hydrogenation over Pt, Pd, or Ni would satutate the recovered and purified compound to the potent dihydro version. Hydrogenation over Pt or Pd in dilute acetic acid give 93% to 97% yields. This product would be 14-hydroxydihydrocodeinone or Oxycodone, either as the dichromate or possibly acetyl salt.

What I like about this procedure is that it is simple and fast and uses only very available reagents.

What I don't like about it is that no yields are stated.

Ref:
1.Chemistry of the Opium Alkaloids, L. small and R. Lutz, US Gov printing office, 1932, pg 259
2.Merk and Co, DRP 411530
3. Frdl 12,750
4. Houben 4, 572


 
drone 342
Member   posted 05-24-98 04:35 PM          
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...And demthylation of the phenol leads in good yields to a considerably stronger product --hydromorphone. I wonder, how much would acylation improve the quality of such a product?
-drone #342


drone 342
Member   posted 05-24-98 04:35 PM          
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...And demthylation of the phenol leads in good yields to a considerably stronger product --hydromorphone. I wonder, how much would acylation improve the quality of such a product?
-drone #342


drone 342
Member   posted 05-24-98 04:38 PM          
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Whoops! That should read "acetylation", not "acylation", and "acetyl", not "acyl".
feeling a bit foolish,

-drone #342


drone 342
Member   posted 05-24-98 04:38 PM          
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Whoops! That should read "acetylation", not "acylation", and "acetyl", not "acyl".
feeling a bit foolish,

-drone #342


David
unregistered   posted 05-24-98 05:03 PM           
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I just did a search on altavista for HYDROXYCODEINONE and came up with nothing. What is this stuff??
(yes, i'm too damn lazy to look it up)


David
unregistered   posted 05-24-98 05:03 PM           
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I just did a search on altavista for HYDROXYCODEINONE and came up with nothing. What is this stuff??
(yes, i'm too damn lazy to look it up)


Cheapskate
Member   posted 05-26-98 08:19 PM          
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Could you expand on simple hydrogenation?
 
Cheapskate
Member   posted 05-26-98 08:19 PM          
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Could you expand on simple hydrogenation?
 
Lone Ranger
unregistered   posted 05-26-98 09:59 PM           
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Sure. The substrate is dissolved in a protonic solvent, such as CH3COOH, and placed in a reaction vessel with a catalytic amount (small) of Pd or Pt on a suitable substrate (ie 5%Pd/C), and shaken or stirred magnetically. H2 uptake is monitored (A graduated cylinder inverted in a water bath). The reaction is complete when H2 uptake ceases. The hydrogen is measured by reading the water level in the inverted cylinder. No heat is needed, as this is a simple ring saturation. Raney nickel is OK, but I do not have (off hand) the yield for this catalyst. It is 97% with Pd, 93% with Pt.
Another nice reaction, as nothing happens until the stirrer is turned on. At that time the water level rises (to replace the comsumed H2)at an almost visible rate.


Lone Ranger
unregistered   posted 05-26-98 09:59 PM           
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Sure. The substrate is dissolved in a protonic solvent, such as CH3COOH, and placed in a reaction vessel with a catalytic amount (small) of Pd or Pt on a suitable substrate (ie 5%Pd/C), and shaken or stirred magnetically. H2 uptake is monitored (A graduated cylinder inverted in a water bath). The reaction is complete when H2 uptake ceases. The hydrogen is measured by reading the water level in the inverted cylinder. No heat is needed, as this is a simple ring saturation. Raney nickel is OK, but I do not have (off hand) the yield for this catalyst. It is 97% with Pd, 93% with Pt.
Another nice reaction, as nothing happens until the stirrer is turned on. At that time the water level rises (to replace the comsumed H2)at an almost visible rate.


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