Phosphorus oxychloride → Ecgonine

HRID 1604009Notes

Reaction equation

HRID 1604009 reaction equation
CN1C2C(C(O)=O)=CCC1CC2.[CH3:13][N:14]1[C@H:18]2[C@@H:19]([C:31]([O:33]C)=[O:32])[C@@H:20]([O:22]C(C3C=CC=CC=3)=O)[CH2:21][C@@H:15]1[CH2:16][CH2:17]2.P(Cl)(Cl)(Cl)=O>Cl>[CH3:13][N:14]1[C@H:18]2[C@@H:19]([C:31]([OH:33])=[O:32])[C@@H:20]([OH:22])[CH2:21][C@@H:15]1[CH2:16][CH2:17]2

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 1017098-Methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylic acidHCID 446220Cocaine2×

Product 1

HCID 91460Ecgonine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

In later references Anhydroecgonine and esters thereof have been prepared by hydrolysis of cocaine in aqueous hydrochloric acid followed by dehydration with phosphorus oxychloride (J. Amer. Chem. Soc., 82 (1960), page 4643 and EP-A1-604 355 ). Although both the hydrolysis of cocaine and the dehydration of ecgonine produces high yields, it is a serious drawback to this method that the reaction mixture becomes syrupy during the dehydration step which makes stirring almost impossible. Using SOCl2 as dehydrating agent causes similar problems.

Sources & evidence

ORD record
ord-0b0afd82917d41c289a2c5d583fb1261
Source dataset
uspto-grants-1999_11
Patent number
US05990312

Reaction notes

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