Hydrochloric Acid → Oxymorphone Hydrochloride

HRID 2262670Notes

Reaction equation

[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3=[CH:8][CH:9]=[C:10]([OH:22])[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]=43)[CH2:4][CH2:3]1)=[O:15].[ClH:23]>[Pd].O>[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3=[CH:8][CH:9]=[C:10]([OH:22])[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]=43)[CH2:4][CH2:3]1)=[O:15].[ClH:23]

Participants

Conditions

Temperature: 60 °C

Procedure

A reaction vessel is charged with 50.1 g of oxymorphone base, prepared as in Example 1.2B, together with 120 g of absolute alcohol. The mixture is heated to 60±2° C. and stirred to form a slurry. A hydrochloric acid solution prepared from 32.7 g concentrated hydrochloric acid and 33.6 g of water is added to the oxymorphone base slurry and the pH is checked to ensure that it is <1.0. 2.0 g of 10% Pd on carbon catalyst water-wet paste is added under a stream of nitrogen to the reaction mixture and the mixture is hydrogenated at 35 psi (2.41 bar) for 20 hours whilst maintaining a temperature of 65° C. The reaction mixture is filtered whilst hot through Celite. The filtrate is cooled to 0-5° C. over 2-3 hours, and stirred for a further 2 hours to form oxymorphone hydrochloride as a precipitate. The precipitate is filtered off, washed with absolute alcohol and then dried to afford white crystals in 77% yield.

Workup

customto form a slurry
temperaturewhilst maintaining a temperature of 65° C
filtrationThe reaction mixture is filtered whilst hot through Celite
temperatureThe filtrate is cooled to 0-5° C. over 2-3 hours
stirringstirred for a further 2 hours

Sources & evidence

ORD record: ord-2f4f90c28168439aa35e309f6f490ba5
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851482B2

Reaction notes

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