Water → Codeine

HRID 34988

Reaction equation

HRID 34988 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+].O>[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

6

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 5288826Morphine

Product 1

HCID 5284371CodeineYield 95.6%

Reagents, catalysts & solvents 2

HCID 67309Phenyltrimethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

Morphine of 89.0% purity 320 parts (1 mole part), potassium carbonate 552 parts (4 moles part), water 65 parts and trimethylphenylammonium chloride 188 parts (1.1 moles part) are heated under stirring in toluene (4000 parts) at 45° to 120° C. for 2 to 8 hrs. to yield 296 parts codeine (95.6% yield after workup as in Example 1.

Sources & evidence

ORD record
ord-de6aa70261ab4783b10797d3fce05e0e
Source dataset
uspto-grants-1988_08
Patent number
US04764615

Linked notes

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