Hydrochloric Acid → Oxycodone Hydrochloride

HRID 589931Notes

Reaction equation

HRID 589931 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].[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]([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:24]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 5284603Oxycodone

Product 1

HCID 5462350Oxycodone HydrochlorideYield 93%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

As described above, oxycodone base purified (Lot P, 13.56 g, 43.0 mmol) was dissolved (in 80-mL beaker over 15 minutes) in the mixture of water (13 mL) and acetic acid (3.0 mL) at ambient temperature. Hydrochloric acid (10.41 mol/kg, 5.0 g or 51.6 mmol) was added to the solution over 5 minutes. Stirring was continued for another 40 minutes and IPA (55 mL) was added over 15 minutes. Stirring was continued for another 30 minutes. Precipitated product was filtered off, washed on filter with IPA (2×20 ml) and acetone (2×20 mL), dried on filter providing 14.74 g oxycodone HCl (39.86 mmol or 93% yield on OC base purified)—lot Q.

Workup

  1. custompurified (Lot P, 13.56 g, 43.0 mmol)
  2. dissolutionwas dissolved (in 80-mL beaker over 15 minutes)
  3. additionin the mixture of water (13 mL) and acetic acid (3.0 mL) at ambient temperature
  4. stirringStirring
  5. waitwas continued for another 30 minutes
  6. filtrationPrecipitated product was filtered off
  7. washwashed
  8. filtrationon filter with IPA (2×20 ml) and acetone (2×20 mL)
  9. customdried
  10. filtrationon filter

Sources & evidence

ORD record
ord-72550233730944b89e27fc628fa1ea43
Source dataset
uspto-grants-2016_01
Patent number
US09233972B2

Reaction notes

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