Hydrochloric Acid → HCID 86590496, compound

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Reaction Steps

The ketone, 2β-(1-Propanoyl)-3β-(4-fluorophenyl)tropane, is dissolved in an appropriate organic solvent such as methanol and then at room temperature the desired alkyl-hydroxyl-amine, such as methyl-hydroxyl-amine, is added in excess (1.01 to 10 equivalents but preferably 5 equivalents). This amine is added as its hydrochloride or as a free base. If a salt is used such as a hydrochloride then an equivalent amount of mild base should be added, such as potassium bicarbonate or other equivalent salt in order to neutralize the amine hydrochloride. If necessary the solution is boiled until reaction occurs, typically 15 minutes to 24 hours is needed. The desired oxime, 1-[3-(4-Fluoro-phenyl)-8-methyl-8-aza-bicyclo[3.2.1]oct-2-yl]-propan-1-one O-methyl-oxime is isolated as an E, Z-mixture and if so desired separated by flash silica gel chromatography to provide either the pure E or pure Z-compound. The pH of the reaction solution is most preferably about 4 but may range from 1-12. See, for example, Morgan et al. J. Am. Chem. Soc. 1994, 116(8),3251-3260.

Provenance & Evidence