Hydrocodone → Oxycodone

HRID 2196375Notes

Reaction equation

[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([O:21][CH3:22])=[C:11]4[O:12][C@H:13]5[C:14]([CH2:16][CH2:17][C@@H:18]2[C@:5]5([C:6]=34)[CH2:4][CH2:3]1)=[O:15].CN1[C@@H]2CC3=CC=C(O)C4[O:34][C@H]5C(CC[C@@H]2[C@]5(C=43)CC1)=O.C1C2C[C@H]3N(CC[C@@]45[C@H]3C=C[C@H](O)[C@@H]4OC(C=25)=C(O)C=1)C>>[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([O:21][CH3:22])=[C:11]4[O:12][C@H:13]5[C:14]([CH2:16][CH2:17][C@:18]2([OH:34])[C@:5]5([C:6]=34)[CH2:4][CH2:3]1)=[O:15]

Participants

Reactant 3

HCID 5284569Hydrocodone

HCID 5284570Hydromorphone

HCID 5288826Morphine

Product 1

HCID 5284603Oxycodone

Procedure

To a 150 mL beaker was charged 10.0 g oxycodone hydrochloride and 100 mL water. Concentrated ammonium hydroxide (2.6 grams) was then added to bring the pH to approximately 9. The product was collected by vacuum filtration, washed with cold water and dried for about 5 hours under vacuum to provide 8.3 g (93% yield) of a white solid consistent in structure with oxycodone free base. This procedure was used to prepare hydrocodone, hydromorphone and morphine free base as needed.

Sources & evidence

ORD record: ord-34a3cf1174fb4095b6e95b615a7e7e95
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338444B1

Reaction notes

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