Hydrochloric Acid → Oxycodone Hydrochloride

HRID 860772Notes

Reaction equation

HRID 860772 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]>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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 5284603Oxycodone

Product 1

HCID 5462350Oxycodone Hydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
73 °C

Procedure

0.8 g of oxycodone base produced in Example 2a was added to a 50 ml flask. Water (1.6 ml) and isopropanol (3.76 ml) were added. Concentrated hydrochloric acid (0.32 ml) was added and the mixture was heated to 73° C. After 5 minutes at 73° C. the mixture was cooled to room temperature and was then stirred at room temperature for 1 hour. The mixture was placed in an ice bath and stirred for 1.5 hours. The solid product was filtered, rinsed with cold isopropanol and dried under a vacuum pump overnight. The product was oxycodone hydrochloride (0.892 g) and contained approximately 5 ppm 14-hydroxycodeinone (measured by MS-SIM).

Workup

  1. temperatureAfter 5 minutes at 73° C. the mixture was cooled to room temperature
  2. customThe mixture was placed in an ice bath
  3. stirringstirred for 1.5 hours
  4. filtrationThe solid product was filtered
  5. washrinsed with cold isopropanol
  6. customdried under a vacuum pump overnight

Sources & evidence

ORD record
ord-6f61e65fb49b482b94341c45b1bb0694
Source dataset
uspto-grants-2006_12
Patent number
US07153966B2

Reaction notes

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