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ChemicalBook CAS DataBase List OXYCODONE HYDROCHLORIDE
124-90-3

OXYCODONE HYDROCHLORIDE synthesis

4synthesis methods
-

Yield:124-90-3 78%

Reaction Conditions:

Stage #1:thebaine with formic acid;dihydrogen peroxide in water at 0 - 80;
Stage #2: with formic acid;hydrogen;5%-palladium/activated carbon in water;isopropyl alcohol at 100; under 30003 Torr; for 16 h;Autoclave;
Stage #3: with hydrogenchloride in water;isopropyl alcoholProduct distribution / selectivity;

Steps:

1
Example 1: Preparation of oxycodone; Thebaine (67 g, 0.215 mol) was dissolved in formic acid (98-100%, 120 g) and hydrogen peroxide (30% in water, 24.5 g, 0.216 mol) added at 0°C. The mixture was pumped continuously at 2 ml/min through a 30 ml continuous flow reactor at 80°C (15 min residence time). An analytical control after the continuous reactor showed less than 1% Thebaine remaining. The continuous stream was added directly to the hydrogenation autoclave that was precharged with 2-propanol (204 g), formic acid (98-100%, 64 g) and 5% Pd/C (7.6 g) and held at 100°C under H2 (40 bar). The hydrogenation was stirred for 16 h. After the hydrogenation, the catalyst was filtered off and the crude mixture was either basified with NaOH to obtain the low impurity Oxycodone base, or treated with HCl in 2-Propanol to give the Oxycodone HCl. The yields were 82% for the base and 78 % for the HCl salt. The 14-Hydroxycodeinone content of the base was 49 ppm and of the HCl salt 29 ppm.

References:

Siegfried Ltd. EP2377866, 2011, A1 Location in patent:Page/Page column 6

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