Hydrochloric Acid → Oxymorphone Hydrochloride

HRID 1043869Notes

Reaction equation

HRID 1043869 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].O.[ClH:24]>CC(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:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 5284604Oxymorphone

Product 1

HCID 5359390Oxymorphone Hydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Conditions

Temperature
70 °C

Procedure

Oxymorphone free base (5.0027 g) was combined with water (2.5 mL) and 2-propanol (6.0 mL) in a round bottom flask (250 mL). The resulting mixture was heated in a temperature controlled bath, with stirring, from ambient to 60° C. over a time period of approximately 30 minutes. Concentrated hydrochloric acid (1.8 mL) was added with continued stirring. The temperature was increased to 70° C. resulting in a clear solution and then cooled to 60° C. 2-propanol was added in 3-5 mL aliquots over approximately 5 minute time span. Solids were observed after the addition of the second aliquot. The resulting slurry was cooled from 60 to 5° C. over 190 minutes and stirred at 5° C. for 45 minutes. Tan solids in a brown solution were observed. The flask was removed from the bath, the contents were vacuum filtered and the solids rinsed 5 times with 1 mL aliquots of 2-propanol:water (9:1 v:v). The resulting white solids were allowed to air-dry for 2 days to yield Form B oxymorphone HCl.

Workup

  1. temperatureThe resulting mixture was heated in a temperature
  2. customambient to 60° C.
  3. customover a time period of approximately 30 minutes
  4. customresulting in a clear solution
  5. temperaturecooled to 60° C
  6. additionafter the addition of the second aliquot
  7. temperatureThe resulting slurry was cooled from 60 to 5° C. over 190 minutes
  8. stirringstirred at 5° C. for 45 minutes
  9. customThe flask was removed from the bath
  10. filtrationfiltered
  11. washthe solids rinsed 5 times with 1 mL aliquots of 2-propanol:water (9:1 v:v)
  12. customto air-dry for 2 days

Sources & evidence

ORD record
ord-aa437aa4aa914b628eeb81da51943844
Source dataset
uspto-grants-2013_10
Patent number
US08563571B2

Reaction notes

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