Oxycodone → Oxycodone Hydrochloride

HRID 1790728Notes

Reaction equation

HRID 1790728 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].[ClH:24].C(O)C>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:24]

Participants

4

Reactant 2

HCID 5284603OxycodoneHCID 21887872Ethanol hydrochloride

Product 1

HCID 5462350Oxycodone Hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A known amount of oxycodone (2.80 g) is charged into a 100 mL round-bottom flask equipped with a magnetic stirrer, a reflux condenser, and a thermometer. Into this, 11 g of anhydrous ethanol is added. This is heated to reflux to form a white suspension. Into this hot suspension, 2.75 g of hydrochloride-ethanol solution (4.85 M) is added in one portion. The resulting clear solution is stirred under reflux for 30 minutes. Heating is stopped and the solution is cooled initially to room temperature, and then to 0–5° C. for 2 h. A white precipitate of oxycodone hydrochloride is formed, which is isolated by filtration. The filter cake is washed with 7.8 g of 2-propanol and vacuum-dried for 3 h to yield oxycodone hydrochloride (2.634 g, 84%) of high purity (>99.5%). The amount of final product in the mother liquor corresponded to approximately 10% yield and the purity of the same is greater than 95%.

Workup

  1. customequipped with a magnetic stirrer, a reflux condenser
  2. temperatureThis is heated
  3. temperatureto reflux
  4. customto form a white suspension
  5. temperatureunder reflux for 30 minutes
  6. temperatureHeating

Sources & evidence

ORD record
ord-4f04d2a2c56b4b278b7210afb01bb875
Source dataset
uspto-grants-2006_07
Patent number
US07071336B2

Reaction notes

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