Water → Oxymorphone

HRID 1513323Notes

Reaction equation

HRID 1513323 reaction equation
[CH3:1][N:2]1[C@@H:18]2[CH2:19][C:7]3[CH:8]=[CH:9][C:10]([OH:22])=[C:11]4[O:12][C@H:13]5[C:14]([O:20]C)=[CH:15][CH:16]=[C:17]2[C@:5]5([C:6]=34)[CH2:4][CH2:3]1.[OH2:23]>>[CH3:1][N:2]1[C@@H:18]2[CH2:19][C:7]3=[CH:8][CH:9]=[C:10]([OH:22])[C:11]4[O:12][C@H:13]5[C:14]([CH2:15][CH2:16][C@:17]2([OH:23])[C@:5]5([C:6]=43)[CH2:4][CH2:3]1)=[O:20]

Participants

3

Reactant 2

HCID 962WaterHCID 5462306Oripavine

Product 1

HCID 5284604Oxymorphone

Procedure

The wet cake was charged to a flask. Water (8×1 g per g of oripavine) was charged. Agitation was turned on and nitrogen sweep was initiated. c-HCl (0.3 mL per g of oripavine) was added to form a solution (pH=about 4 to 5). A charcoal treatment and filtration was conducted when the color was dark. c-NH4OH (˜1 mL per g of oripavine) was added to adjust pH=about 9 to 10 to form a precipitate. The mixture was stirred at room temperature for 1 hour, then was filtered and washed with water (5×1 mL per g of oripavine). The resulting solid was dried under flowing air at room temperature or 1 hour to give a solid. The solid was further dried under house vacuum at 75° C. for 16 hours to give the product as a tan solid. The weight of solid should range from 0.8 g to 1.0 g per g of oripavine with peak area >95%, wt/wt 90 to 95% and water content 3 to 5%.

Workup

  1. filtrationA charcoal treatment and filtration
  2. additionc-NH4OH (˜1 mL per g of oripavine) was added
  3. customto form a precipitate
  4. filtrationwas filtered
  5. washwashed with water (5×1 mL per g of oripavine)
  6. customThe resulting solid was dried
  7. customat room temperature
  8. custom1 hour to give a solid
  9. customThe solid was further dried under house vacuum at 75° C. for 16 hours
  10. customto give the product as a tan solid

Sources & evidence

ORD record
ord-07e0f95b47c7429195863e741d0009ca
Source dataset
uspto-grants-2012_07
Patent number
US08217175B2

Reaction notes

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