Sodium Hydroxide → Codeine

HRID 2370091Notes

Reaction equation

HRID 2370091 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.O.OP(O)(O)=O.[OH-].[Na+]>O>[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

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9953630Codeine phosphate hydrate

Product 1

HCID 5284371CodeineYield 78.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1 g (2.52 mmol) of codeine phosphate was dissolved in 60 mL of water and then 30% NaOH solution was added dropwise until the pH of the solution reached 10. Codeine free base precipitated out at this pH. Codeine free base was extracted with chloroform 5 times from the aqueous layer. Chloroform layers were combined, dried over anhydrous Na2SO4, filtered and then concentrated under vacuum to get 0.59 g (78% yield) of codeine free base as a white solid.

Workup

  1. customCodeine free base precipitated out at this pH
  2. extractionCodeine free base was extracted with chloroform 5 times from the aqueous layer
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-91f40f7b643845b58213dfb8295f84a1
Source dataset
uspto-grants-2014_04
Patent number
US08710069B2

Reaction notes

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