Potassium Carbonate → Codeine

HRID 34990

Reaction equation

HRID 34990 reaction equation
[CH:1]1[C:17]2[CH2:16][C@H:15]3[N:18]([CH2:20][CH2:21][C@@:7]45[C@H:14]3[CH:13]=[CH:12][C@H:10]([OH:11])[C@@H:8]4[O:9][C:5]([C:6]=25)=[C:3]([OH:4])[CH:2]=1)[CH3:19].[C:22](=O)([O-])[O-].[K+].[K+]>[Cl-].C[N+](C)(C)C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH3:19][N:18]1[C@@H:15]2[CH2:16][C:17]3[CH:1]=[CH:2][C:3]([O:4][CH3:22])=[C:5]4[O:9][C@H:8]5[C@@H:10]([OH:11])[CH:12]=[CH:13][C@@H:14]2[C@:7]5([C:6]=34)[CH2:21][CH2:20]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 5288826Morphine

Product 1

HCID 5284371CodeineYield 98%

Reagents, catalysts & solvents 2

HCID 67309Phenyltrimethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

Morphine of 89% purity 320 parts (1 mole part), potassium carbonate 414 parts (3 moles part) and trimethylphenyl-ammonium chloride 188 parts (1.1 moles part) are heated under stirring in toluene (4000 parts) at 45°-110° C. for 3-8 hrs. to yield 293 parts of codeine (98.0% yield), after workup as in Example 1.

Sources & evidence

ORD record
ord-63cc52c60dae41f2b09880a3ea603c87
Source dataset
uspto-grants-1988_08
Patent number
US04764615

Linked notes

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