Codeine → Hydrocodone

HRID 1293509Notes

Reaction equation

HRID 1293509 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.[Pd]>[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

4

Reactant 1

HCID 5284371Codeine

Product 1

HCID 5284569HydrocodoneYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 1.2 g (4.0 mmol) of codeine in 40 mL of methanol was added 100 mg of 10% Pd—C. The resulting reaction mixture was hydrogenated under pressure of 50 psi. The solution was filtered through CELITE (Celite Corporation), and the filtrate was concentrated to give 1.12 g (3.7 mmol, 93%) of dihydrocodeinone as a white solid. ES (+) m/z 301.

Workup

  1. customThe resulting reaction mixture
  2. filtrationThe solution was filtered through CELITE (Celite Corporation)
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-02d9d0de15174fdba27c036200f47436
Source dataset
uspto-grants-2007_07
Patent number
US07238791B1

Reaction notes

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