Hydrochloric Acid → Oxycodone Hydrochloride

HRID 254843

Reaction equation

HRID 254843 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].CN1[C@@H]2CC3C=CC(OC)=C4OC5C(C=C[C@]2(O)[C@]5(C=34)CC1)=O.O.[ClH:48]>C(O)CCC.[Zn]>[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:48]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 5284603OxycodoneHCID 5359420(4R,4aS,12bS)-4a-hydroxy-9-methoxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one

Product 1

HCID 5462350Oxycodone Hydrochloride

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 2631-ButanolSolvent

Conditions

Temperature
20 °C

Procedure

Oxycodone base (40.07 g) containing 4869 ppm of 14-hydroxycodeinone and 13.7 ppm DHDHC, was suspended in 1-butanol (250 mL) and water (180 mL) in a jacketed reactor. At 15° C. and with the reaction under nitrogen, aqueous hydrochloric acid (37%) was added to achieve a pH of 2.86. At 25° C., zinc dust (1 g) was added and the resulting mixture was stirred for 3 hr (Note: pH increased to 5.86 upon zinc powder addition). Activated carbon (Norit KB-G, 4 g) was added to the reactor and the solution was allowed to stir for 40 min. The reaction mixture was then filtered to remove the zinc and carbon. The filtrate was charged to a clean reactor. The pH of the solution was adjusted to 6.17 using pyridine (15 mL). Water was distilled off under vacuum at 60° C. The solution was then cooled to 20° C. and allowed to stir for 15 min. The solids were filtered and washed with 1-butanol (20 mL×2). The product was dried to a constant weight at 65° C. under vacuum to yield 42.14 g of crude oxycodone hydrochloride.

Workup

  1. customAt 15° C. and with the reaction under nitrogen
  2. additionActivated carbon (Norit KB-G, 4 g) was added to the reactor
  3. stirringto stir for 40 min
  4. filtrationThe reaction mixture was then filtered
  5. customto remove the zinc and carbon
  6. additionThe filtrate was charged to a clean reactor
  7. distillationWater was distilled off under vacuum at 60° C
  8. stirringto stir for 15 min
  9. filtrationThe solids were filtered
  10. washwashed with 1-butanol (20 mL×2)
  11. customThe product was dried to a constant weight at 65° C. under vacuum

Sources & evidence

ORD record
ord-5e9efb52220b43b786c2ac7e65f0416e
Source dataset
uspto-grants-2011_01
Patent number
US07875719B2

Linked notes

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