Hydrochloric Acid → Codeinone
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.CN1[C@@H]2CC3C=CC(OC)=C4O[C@H]5[C@@H](O)C=C[C@@H]2[C@]5(C=34)CC1.O.OP(O)(O)=O.Cl>>[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]([CH:15]=[CH:16][C@@H:17]2[C@:5]5([C:6]=34)[CH2:4][CH2:3]1)=[O:20]Participants
Procedure
A solution of codeine or codeine phosphate was dissolved in the appropriate solvent system and a specified volume of hydrochloric acid of varying concentration was added. Manganese dioxide (either freshly prepared γ-manganese dioxide or activated manganese dioxide from Aldrich) was added and the reaction mixture was stirred at ambient temperature for 1.5 to 4 hours. The progress of the reaction was monitored by HPLC. The reaction mixture was filtered through a celite pad, washed with additional solvent or water, and neutralised with ammonium hydroxide. The product was extracted with methylene chloride (3×150 ml) and the combined extracts washed with water and dried over anhydrous sodium sulphate. The organic layer was then evaporated to yield codeinone.
Workup
- concentrationconcentration
- additionwas added
- additionManganese dioxide (either freshly prepared γ-manganese dioxide or activated manganese dioxide from Aldrich) was added
- filtrationThe reaction mixture was filtered through a celite pad
- washwashed with additional solvent or water
- extractionThe product was extracted with methylene chloride (3×150 ml)
- washthe combined extracts washed with water
- dry with materialdried over anhydrous sodium sulphate
- customThe organic layer was then evaporated
Sources & evidence
- ORD record
- ord-5c2445e491fc4d40b9d05c71b55c92df
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06235906B1
Reaction notes
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