Methods of synthesizing anatabine
AssigneeRock Creek Pharmaceuticals, Inc.
InventorsTom Thomas Puthiaparampil, Thomas Kanathkunn David, Muppala Sarveswara Raju
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Abstract
Anatabine is obtained by reacting benzophenoneimine with 3-aminomethyl pyridine to form benzylhydrylidene-pyridin-3-yl-methyl-amine. The benzylhydrylidene-pyridin-3-yl-methyl-amine is treated with a non-nucleophilic base and a dielectrophile, such as cis-1,4-dichloro-2-butene, followed by acidification, then basification, to provide anatabine. The resulting anatabine is substantially free from contaminants and displays good stability. In an alternative embodiment, the benzylhydrylidene-pyridin-3-yl-methyl-amine may be used in the synthesis of other alkaloids such as anabasine, nornicotine, N-methylanabasine, and anabaseine.
Claims15
A method of preparing benzylhydrylidene-pyridin-3-yl-methyl-amine, comprising reacting 3-aminomethylpyridine with benzophenoneimine to obtain a compound of Formula I:
A method of synthesizing anatabine comprising the steps of:
- (a) reacting 3-aminomethylpyridine with benzophenoneimine to obtain a compound of Formula I:
- (b) reacting the compound of Formula I with a non-nucleophilic base and a dielectrophile to obtain a compound of Formula II:
- wherein X is a halogen,
- (c) treating the compound of Formula II with an acid to obtain a compound of Formula III:
- wherein X is a halogen;
- and
- (d) treating the compound of Formula III with at least one base to obtain anatabine.
A method of recovering anatabine from a reaction product, comprising contacting the reaction product with methyl tert-butyl ether (MTBE) under distillation.
A method of synthesizing an alkaloid comprising:
- (a) reacting 3-aminomethylpyridine with benzophenoneimine to obtain a compound of Formula I:
- (b) reacting the compound of Formula I with a non-nucleophilic base and a dielectrophile to obtain a compound of Formula IIa:
- (c) treating the compound of Formula IIa with an acid to obtain a compound of Formula IIIA:
- and
- (d) treating the compound of Formula IIIa with at least one base to obtain the alkaloid.
An acceptable pharmaceutical, dietary supplement or food grade salt of anatabine.
Dependencies are inferred from the claim text.