gamma-Cyclodextrine → Codeine

HRID 1383798

Reaction equation

HRID 1383798 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.C([O-])(=O)CCCCCCCCCCC.C(O)[C@H]1O[C@@H]2O[C@H]3[C@H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@@H](O[C@H]5[C@H](O)[C@@H](O)C(OC6[C@H](O)[C@@H](O)C(C7[C@H](O)[C@@H](O)C(O[C@H]8[C@H](O)[C@@H](O)[C@@H](O[C@H]9[C@H](O)[C@@H](O)[C@@H](O[C@H]1[C@H](O)[C@H]2O)O[C@@H]9CO)O[C@@H]8CO)O[C@@H]7CO)O[C@@H]6CO)O[C@@H]5CO)O[C@@H]4CO)O[C@@H]3CO>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 44431027gamma-Cyclodextrine2×HCID 86757113Codeine laurate2×

Product 1

HCID 5284371Codeine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Codeine laurate and gamma-cyclodextrin were complexed by the kneading method. Codeine laurate (0.700 g) and gamma-cyclodextrin (1.754 g) were blended together. Water (2.5 mL) was added and the mixture ground together in a mortar with a pestle to form a uniform paste. Grinding was continued for 30 minutes. The paste was then dried in a vacuum oven (40° C.; 0 bar) for 48 hours. The solid mass was broken up, passed through a 60 mesh screen and returned to the vacuum oven (40° C.; 0 bar) for 12 hours in order to ensure uniform drying of the complex. Analysis by HPLC for codeine base content, and Karl Fischer for moisture content gave the following results: % codeine base was 16.08%, and the moisture content was 8.72%. The complex was characterised by DSC, FT-IR and XRD.

Workup

  1. customthe mixture ground together in a mortar with a pestle to form a uniform paste
  2. customGrinding
  3. customThe paste was then dried in a vacuum oven (40° C.; 0 bar) for 48 hours
  4. waitreturned to the vacuum oven (40° C.; 0 bar) for 12 hours in order
  5. customto ensure uniform drying of the complex

Sources & evidence

ORD record
ord-b2b7969b105047b2a1f4de15570c18c2
Source dataset
uspto-grants-2001_07
Patent number
US06255502B1

Linked notes

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