Codeine → Hydrocodone

HRID 2252277Notes

Reaction equation

HRID 2252277 reaction equation
[CH3:1][N:2]1[C@@H:18]2[CH2:19][C:7]3[CH:8]=[CH:9][C:10]([O:21][CH3:22])=[C:11]4[O:12][C@H:13]5[C@@H:14]([OH:20])[CH:15]=[CH:16][C@@H:17]2[C@:5]5([C:6]=34)[CH2:4][CH2:3]1>CCO>[CH3:1][N:2]1[C@@H:18]2[CH2:19][C:7]3[CH:8]=[CH:9][C:10]([O:21][CH3:22])=[C:11]4[O:12][C@H:13]5[C:14]([CH2:15][CH2:16][C@@H:17]2[C@:5]5([C:6]=34)[CH2:4][CH2:3]1)=[O:20]

Participants

3

Reactant 1

HCID 5284371Codeine

Product 1

HCID 5284569HydrocodoneYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Codeine, 5.0 g, and 0.117 g catalyst, Ru(P(C6H5)3)3Cl2, were dissolved in 25 ml EtOH. The mixture was flushed with nitrogen for 5 minutes. After refluxing under nitrogen for 2 hours the reaction mixture was cooled down to 0° C. and filtered. The collected crystals were washed twice with 5 ml each MeOH and dried in air for 1 hour to yield white crystals, 70% yield hydrocodone.

Workup

  1. customThe mixture was flushed with nitrogen for 5 minutes
  2. temperatureAfter refluxing under nitrogen for 2 hours the reaction mixture
  3. filtrationfiltered
  4. washThe collected crystals were washed twice with 5 ml each MeOH
  5. customdried in air for 1 hour

Sources & evidence

ORD record
ord-647c3cec3b01403da8ce4795ce314d18
Source dataset
uspto-grants-2008_01
Patent number
US07321038B2

Reaction notes

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