Hydrochloric Acid → Oxymorphone Hydrochloride

HRID 2262671Notes

Reaction equation

HRID 2262671 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

5

Reactant 2

HCID 313Hydrochloric AcidHCID 5284604Oxymorphone

Product 1

HCID 5359390Oxymorphone HydrochlorideYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

A reaction vessel is charged with 2.5 g of oxymorphone base, prepared as in Example 2.2B, together with 7.5 mL of absolute alcohol, 2.5 g of water and 1.66 g of concentrated hydrochloric acid. The mixture is heated to 50-60° C. and a solution results. The pH is checked to ensure that it is <1.0. 0.111 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 21 hours whilst maintaining a temperature of 65±3° C. The reaction mixture is filtered whilst hot through a 0.45 μm 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 filtered off, washed with cold absolute alcohol and dried under vacuum to afford white crystals in 77% yield.

Workup

  1. customa solution results
  2. temperaturewhilst maintaining a temperature of 65±3° C
  3. filtrationThe reaction mixture is filtered whilst hot through a 0.45 μm
  4. filtrationfilter
  5. temperatureThe filtrate is cooled to 0-5° C. over 2-3 hours

Sources & evidence

ORD record
ord-e204f57620ed47308d41d0d354ca3d30
Source dataset
uspto-grants-2010_12
Patent number
US07851482B2

Reaction notes

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