Hydrochloric Acid → Oxycodone Hydrochloride

HRID 1790730Notes

Reaction equation

HRID 1790730 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

Procedure

8.1 g of oxycodone obtained in Example 15 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 concentrated 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., 7.7 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-5b665a2b43e14375b34a87ca38617832
Source dataset
uspto-grants-2006_07
Patent number
US07071336B2

Reaction notes

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