Hydrochloric Acid → Oxycodone Hydrochloride

HRID 860773Notes

Reaction equation

HRID 860773 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]>[Pd].C(O)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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 5284603Oxycodone

Product 1

HCID 5462350Oxycodone Hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
75 °C

Procedure

18.8 g oxycodone prepared via Route B was added to a flask containing ethanol (43.9 ml) and water (10.14 ml). Ethanol (5.71 ml) and concentrated hydrochloric acid (7.37 ml) were mixed and then added to the flask, providing a mixture with a pH of 1. The mixture was heated at 75° C. for 5 hours and was then cooled to 65° C. The mixture was hydrogenated at 10–12 psi for six hours using a 10 wt % palladium on carbon catalyst (175.6 mg wet weight, 88 mg dry weight). The mixture was filtered to remove the catalyst and cooled. The solid product was filtered and washed with ethanol. The product was oxycodone hydrochloride (20.13 g, 75.3%) and contained approximately 0 ppm 14-hydroxycodeinone.

Workup

  1. additionwas added to a flask
  2. additionadded to the flask
  3. customproviding a mixture with a pH of 1
  4. temperaturewas then cooled to 65° C
  5. filtrationThe mixture was filtered
  6. customto remove the catalyst
  7. temperaturecooled
  8. filtrationThe solid product was filtered
  9. washwashed with ethanol

Sources & evidence

ORD record
ord-d5ac7c2a62d048c69fcc382ae218ddc4
Source dataset
uspto-grants-2006_12
Patent number
US07153966B2

Reaction notes

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