Hydrochloric Acid → Oxycodone Hydrochloride

HRID 860771Notes

Reaction equation

HRID 860771 reaction equation
[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([O:22][CH3:23])=[C:11]4[O:12][C@H:13]5[C:14]([CH2:16][CH2:17][C@:18]2([OH:21])[C@:5]5([C:6]=34)[CH2:4][CH2:3]1)=[O:15].O.[ClH:25].[H][H]>[Pd].C(O)(C)C>[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([O:22][CH3:23])=[C:11]4[O:12][C@H:13]5[C:14]([CH2:16][CH2:17][C@:18]2([OH:21])[C@:5]5([C:6]=34)[CH2:4][CH2:3]1)=[O:15].[ClH:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 5284603OxycodoneHCID 178418361HCID 178418361, compound

Product 1

HCID 5462350Oxycodone Hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
75 °C

Procedure

5 g of oxycodone product from comparative example 2 was added to a 100 ml flask. Water (10 ml) and isopropanol (10 ml) were added and the mixture was stirred. Concentrated hydrochloric acid (2.64 ml) was added. The mixture was heated to 75° C. for 10 hours and stirred at ambient temperature overnight. The mixture was transferred to a hydrogenation bottle and was heated to 45° C. 5 wt % palladium on carbon catalyst (0.5 g) was added to the mixture and hydrogen was passed through the mixture at about 12 psi for 6.5 hours. The mixture was warmed to 55° C., passed through a filter paper, cooled to room temperature and then placed in an ice bath for 30 minutes. The solid product was filtered, rinsed with cold isopropanol and dried overnight under a vacuum pump. The product was oxycodone hydrochloride (5.533 g, 99.2%) and contained less than 2 ppm 14-hydroxycodeinone (measured by HPLC and MS-SIM (mass spectrometry with selected ion monitoring)).

Workup

  1. stirringstirred at ambient temperature overnight
  2. temperaturewas heated to 45° C
  3. temperatureThe mixture was warmed to 55° C.
  4. temperaturecooled to room temperature
  5. waitplaced in an ice bath for 30 minutes
  6. filtrationThe solid product was filtered
  7. washrinsed with cold isopropanol
  8. customdried overnight under a vacuum pump

Sources & evidence

ORD record
ord-f878033a5414489bb8cfde63aa2a3786
Source dataset
uspto-grants-2006_12
Patent number
US07153966B2

Reaction notes

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