Hydrochloric Acid → Ecgonine methyl ester

HRID 1440977Notes

Reaction equation

HRID 1440977 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.Cl>O>[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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 656832(-)-Cocaine hydrochloride

Product 1

HCID 104904Ecgonine methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Cocaine hydrochloride (2.0 g) was dissolved in distilled water (100 ml) and concentrated hydrochloric acid (8.0 ml) and refluxed for 19 hours. After cooling to room temperature, the benzoic acid precipitated and was filtered. The filtrate was washed with chloroform to remove any remaining benzoic acid. The aqueous solution was evaporated to dryness in vacuo. The residue (ecgonine hydrochloride) was esterified by refluxing in methanolic hydrogen chloride (150 ml) for 17 hours. The solvent was removed in vacuo to yield ecgonine methyl ester as an oil.

Workup

  1. customthe benzoic acid precipitated
  2. filtrationwas filtered
  3. washThe filtrate was washed with chloroform
  4. customto remove any remaining benzoic acid
  5. customThe aqueous solution was evaporated to dryness in vacuo
  6. temperatureby refluxing in methanolic hydrogen chloride (150 ml) for 17 hours
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-28ec9451232f47f78445d3a22fdfc220
Source dataset
uspto-grants-1996_03
Patent number
US05501985

Reaction notes

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