Ammonia → Oxycodone Hydrochloride

HRID 860774Notes

Reaction equation

HRID 860774 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].C(O)C.[ClH:27].N>[Pd].O>[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:27]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 702EthanolHCID 5284603Oxycodone

Product 1

HCID 5462350Oxycodone Hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

4.35 g oxycodone prepared by essentially the same method as Route B was added to a flask containing ethanol (12.5 ml) and water (2.7 ml). Concentrated hydrochloric acid (approximately 1.5 ml) was added to the flask, providing a mixture with a pH of about 2. The pH of the mixture was increased to 5 by adding ammonia. The mixture was hydrogenated at 45 psi and 50° C. for 1.5 hours and then at 10–12 psi and 50–55° C. for 4 hours using a 10 wt % palladium on carbon catalyst (0.06 g). The mixture was filtered to remove the catalyst and cooled. The solid product was filtered and washed with ethanol. The product was oxycodone hydrochloride (3.706 g, 76.1%) and contained approximately 12 ppm 14-hydroxycodeinone.

Workup

  1. additionwas added to a flask
  2. customproviding a mixture with a pH of about 2
  3. temperatureThe pH of the mixture was increased to 5
  4. waitat 10–12 psi and 50–55° C. for 4 hours using
  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-2e3d3d61b77047a9be158818cbac8726
Source dataset
uspto-grants-2006_12
Patent number
US07153966B2

Reaction notes

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