Hydrocodone → Oxycodone

HRID 1046348Notes

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-7bfe11b935d84ec2b98981c142dc1478
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569330B1

Reaction notes

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