Codeine → Hydrocodone

HRID 748601Notes

Reaction equation

HRID 748601 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>CO>[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 5284569Hydrocodone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
7 °C

Procedure

A 100 mL Schlenk tube was charged with methanol (30 mL) and codeine free base (5.3 g, 17.7 mmol). The stirred solution was heated to reflux under nitrogen for 15 min and treated with the solution of the catalyst added by a pipette. The resulting brown solution was stirred and heated to reflux under nitrogen for 1 hour, cooled to 7° C. in an ice bath, stirred at this temperature for another 30 min and filtered. The filtered solid was washed with cold isopropanol (3×6 mL) and dried in an oven at 95° C. to give hydrocodone free base as a white solid. The yield was 4.48 g, 84.5%.

Workup

  1. temperatureThe stirred solution was heated
  2. temperatureto reflux under nitrogen for 15 min
  3. additiontreated with the solution of the catalyst
  4. additionadded by a pipette
  5. temperatureheated
  6. temperatureto reflux under nitrogen for 1 hour
  7. stirringstirred at this temperature for another 30 min
  8. filtrationfiltered
  9. washThe filtered solid was washed with cold isopropanol (3×6 mL)
  10. customdried in an oven at 95° C.

Sources & evidence

ORD record
ord-195ab8ab06074fc299f208a273dda7cd
Source dataset
uspto-grants-2008_07
Patent number
US07399859B1

Reaction notes

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