Hydrocodone → Oxycodone

HRID 1409550Notes

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-9131471aec1b4914b3cf719cff262626
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921386B1

Reaction notes

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