Cocaine → Ecgonine methyl ester

HRID 1590031Notes

Reaction equation

HRID 1590031 reaction equation
[CH3:1][N:2]1[C@H:6]2[C@@H:7]([C:19]([O:21][CH3:22])=[O:20])[C@@H:8]([O:10]C(C3C=CC=CC=3)=O)[CH2:9][C@@H:3]1[CH2:4][CH2:5]2>Cl>[CH3:1][N:2]1[C@H:6]2[C@@H:7]([C:19]([O:21][CH3:22])=[O:20])[C@@H:8]([OH:10])[CH2:9][C@@H:3]1[CH2:4][CH2:5]2

Participants

3

Reactant 1

HCID 446220Cocaine

Product 1

HCID 104904Ecgonine methyl ester

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Cocaine (Merck) (3.91 g) was dissolved in 100 ml IN HCl and heated to reflux for 19 hours. After cooling to room temperature, the benzoic acid was filtered and washed with water. The water was washed with chloroform several times and the water was removed in vacuo. The residue was dissolved in 200 ml anhydrous methanol and the solution was saturated with HCl gas. The reaction mixture was refluxed for 17 hours. After cooling to room temperature, the solvent was removed in vacuo. The residue was dissolved in water and basified with potassium carbonate to pH 9. The basic water was extracted with methylene chloride several times. After drying the organic layer over sodium sulfate, the solvent was removed in vacuo to yield ecgonine methyl ester as an oil.

Workup

  1. temperatureheated
  2. temperatureto reflux for 19 hours
  3. filtrationthe benzoic acid was filtered
  4. washwashed with water
  5. washThe water was washed with chloroform several times
  6. customthe water was removed in vacuo
  7. dissolutionThe residue was dissolved in 200 ml anhydrous methanol
  8. temperatureThe reaction mixture was refluxed for 17 hours
  9. temperatureAfter cooling to room temperature
  10. customthe solvent was removed in vacuo
  11. dissolutionThe residue was dissolved in water
  12. extractionThe basic water was extracted with methylene chloride several times
  13. dry with materialAfter drying the organic layer over sodium sulfate
  14. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-44237f2a855d49d9a51f493a8cc3176d
Source dataset
uspto-grants-1993_04
Patent number
US05202270

Reaction notes

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