Hydrochloric Acid → Oxycodone Hydrochloride

HRID 983651Notes

Reaction equation

HRID 983651 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]>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:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 5284603Oxycodone

Product 1

HCID 5462350Oxycodone HydrochlorideYield 85%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
2.5 °C

Procedure

8.1 g of oxycodone obtained in Example 6 and 80 ml of ethanol are placed in a 250 ml round-bottomed flask. The mixture is heated to reflux. Into the hot mixture is added 10 ml of a concenrated solution of hydrogen chloride in isopropanol. The mixture is cooled and stirred at 0-5° C. for 1-2 hours. The product is filtered off and the filter cake is washed with a small amount of cold ethanol. After drying in vacuo (e.g., 50 mm Hg) at 30-40° C., 77 g (85% yield) of pure oxycodone hydrochloride is obtained.

Workup

  1. temperatureThe mixture is heated to reflux
  2. temperatureThe mixture is cooled
  3. filtrationThe product is filtered off
  4. washthe filter cake is washed with a small amount of cold ethanol
  5. customAfter drying in vacuo (e.g., 50 mm Hg) at 30-40° C.

Sources & evidence

ORD record
ord-69400d6065894b839c4c0e07ad5d5466
Source dataset
uspto-grants-2005_03
Patent number
US06864370B1

Reaction notes

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