Hydromorphone → Hydromorphone Hydrochloride

HRID 1357003Notes

Reaction equation

HRID 1357003 reaction equation
[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3=[CH:8][CH:9]=[C:10]([OH:21])[C:11]4[O:12][C@H:13]5[C:14]([CH2:16][CH2:17][C@@H:18]2[C@:5]5([C:6]=43)[CH2:4][CH2:3]1)=[O:15].[ClH:22].O>CO.O>[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3=[CH:8][CH:9]=[C:10]([OH:21])[C:11]4[O:12][C@H:13]5[C:14]([CH2:16][CH2:17][C@@H:18]2[C@:5]5([C:6]=43)[CH2:4][CH2:3]1)=[O:15].[ClH:22]

Participants

4

Reactant 2

HCID 5284570HydromorphoneHCID 21885828Hydrate;hydrochloride

Product 1

HCID 5462347Hydromorphone HydrochlorideYield 30%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

The hydromorphone base (15.0 g) was dissolved in methanol/DI water (14 mL, 50/50 by volume) and concentrated HCl/water (10 mL, 50/50 by volume). The solution was filtered and n-propanol (42 mL) was added. The suspension was stirred overnight, filtered, and vacuum dried. The dried hydromorphone hydrochloride (12.9 g; 30% yield) contained 0.7% 8-hydroxyhydromorphone and 0.1 % dihydromorphine. The hydromorphone hydrochloride failed the Readily Carbonizable Substances Test.

Workup

  1. filtrationThe solution was filtered
  2. additionn-propanol (42 mL) was added
  3. filtrationfiltered
  4. customvacuum dried

Sources & evidence

ORD record
ord-477498e1e90b491dbf73df153b8b157c
Source dataset
uspto-grants-2003_07
Patent number
US06589960B2

Reaction notes

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