Hydrochloric Acid → Oxymorphone Hydrochloride

HRID 515576Notes

Reaction equation

HRID 515576 reaction equation
[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3=[CH:8][CH:9]=[C:10]([OH:22])[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]=43)[CH2:4][CH2:3]1)=[O:15].[ClH:23]>C(O)C>[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3=[CH:8][CH:9]=[C:10]([OH:22])[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]=43)[CH2:4][CH2:3]1)=[O:15].[ClH:23]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 5284604Oxymorphone

Product 1

HCID 5359390Oxymorphone HydrochlorideYield 86.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

Purified oxymorphone (17.8 g, 59 mmol) was suspended in 94% aq. ethanol (107 ml) and stirred at 50-60° C. Concentrated hydrochloric acid (32%) was added slowly to adjust the pH to 2.58. The mixture was allowed to cool to room temperature, and then cooled further to 0-10° C., stirred for 2 hours and filtered then washed with ethanol (3×20 ml). The isolated solids were dried at 75° C. under 25 inches-Hg overnight to give oxymorphone HCl as white solids (17.3 g, 51 mmol, 86.7% yield).

Workup

  1. temperatureto cool to room temperature
  2. temperaturecooled further to 0-10° C.
  3. stirringstirred for 2 hours
  4. filtrationfiltered
  5. washthen washed with ethanol (3×20 ml)
  6. customThe isolated solids were dried at 75° C. under 25 inches-Hg overnight

Sources & evidence

ORD record
ord-c215e29357284e59a5510ad0cb0ccad5
Source dataset
uspto-grants-2015_08
Patent number
US09108974B2

Reaction notes

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