Cocaine → Ecgonine

HRID 1934277Notes

Reaction equation

HRID 1934277 reaction equation
[CH3:1][N:2]1[C@H:6]2[C@@H:7]([C:19]([O:21]C)=[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]([OH:21])=[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 91460EcgonineYield 92%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
112.5 °C

Procedure

Commercially available (−)-cocaine (Sigma Chemical Co.) was dissolved in 1.25 M HCl (1 g cocaine/12 ml). The mixture was allowed to stir for 16 hours at 110-115° C. (gentle reflux). After cooling to room temperature, the mixture was thoroughly extracted with ether to remove the benzoic acid by-product. The acidic aqueous layer was evaporated on a rotary evaporator under high vacuum and then the residue was redissolved in water and lyophilized to afford a white solid that required no further purification (92% yield).

Workup

  1. temperature(gentle reflux)
  2. temperatureAfter cooling to room temperature
  3. extractionthe mixture was thoroughly extracted with ether
  4. customto remove the benzoic acid by-product
  5. customThe acidic aqueous layer was evaporated on a rotary evaporator under high vacuum
  6. dissolutionthe residue was redissolved in water
  7. customto afford a white solid that
  8. customno further purification (92% yield)

Sources & evidence

ORD record
ord-86c8e3c66a1b49beb5ee60635881dccd
Source dataset
uspto-grants-2002_05
Patent number
US06383490B1

Reaction notes

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