Hydrochloric Acid → Oxymorphone Hydrochloride

HRID 2262669Notes

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 1 kg of oxymorphone base, prepared as in Example 1.1B, together with 2.05 kg of absolute alcohol and 0.66 kg of water. The mixture is heated to 60±2° C. and stirred to form a slurry. A hydrochloric acid solution prepared from 0.66 kg concentrated hydrochloric acid, 0.24 kg of water and 0.31 kg of absolute alcohol is added to the oxymorphone base slurry and the pH checked to ensure that it is <1.0. 40 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±5 psi (2.41 bar) for 20 hours whilst maintaining a temperature of 65±3° C. The reaction mixture is filtered whilst hot through Celite and a 0.2 μm polish filter. 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 washed with absolute alcohol then dried. Yield is 80%.

Workup

customto form a slurry
temperaturewhilst maintaining a temperature of 65±3° C
filtrationThe reaction mixture is filtered whilst hot through Celite
filtrationa 0.2 μm polish filter
temperatureThe filtrate is cooled to 0-5° C. over 2-3 hours
stirringstirred for a further 2 hours

Sources & evidence

ORD record: ord-e31cdb2cadbb4810b9f78a823bcf8971
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851482B2

Reaction notes

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