Hydrochloric Acid → Oxycodone Hydrochloride

HRID 2369251Notes

Reaction equation

HRID 2369251 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]>O>[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 91.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

To a 10 mL flask is charged 1.0 g (3.17 mmol, Lot 2377-103) of oxycodone base (from Example 7) 3.2 mL ethanol and 0.63 mL of water. The mixture is stirred at room temperature (RT, 20±5° C.). A slurry is resulted. The batch is heated to 45° C., added 0.326 g (3.31 mmol, 1.044 molar equivalents) of 37% hydrochloric acid, and a solution is then resulted. The mixture is heated to 55° C. and stirred at 55° C. for 10 hours. Cooled to RT and then to 0-5° C. The mixture is stirred at 0-5° C. for 1.5 hours, filtered, rinsed with cold ethanol (2 mL×2) and dried. 1.021 g of oxycodone HCl (91.4% yield, as Lot 2377-107) is obtained. (3 ppm 14-hydroxycodeinone, undetected 8α,14-dihydroxy-7,8-dihydrocodeinone by LC/MS, and 8β,14-dihydroxy-7,8-dihydrocodeinone by LC/MS; 99.84A % pure by HPLC).

Workup

  1. customA slurry is resulted
  2. temperatureThe batch is heated to 45° C.
  3. customa solution is then resulted
  4. temperatureThe mixture is heated to 55° C.
  5. stirringstirred at 55° C. for 10 hours
  6. temperatureCooled to RT
  7. customto 0-5° C
  8. stirringThe mixture is stirred at 0-5° C. for 1.5 hours
  9. filtrationfiltered
  10. washrinsed with cold ethanol (2 mL×2)
  11. customdried

Sources & evidence

ORD record
ord-3c0e2320b8064c8682540237905b82ff
Source dataset
uspto-grants-2014_04
Patent number
US08703950B2

Reaction notes

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