Patent ID: 7524963

Claim:
A compound of the Formula: wherein said compound contains an enriched Z-isomer, with the Z-isomer predominating over the E-isomer by at least about a 90:10 ratio, with said compound being prepared by a process comprising: (a) converting isonipecotic acid (Formula III) to its N-protected derivative (Formula IIIA): where Y is a protecting group; (b) converting the compound of Formula IIIA to its acid halide (Formula IV): (c) reacting said compound of Formula IV with a suitable halobenzene in the presence of a suitable Friedel-Crafts catalyst to yield the compound of Formula V: where X is a halogen; (d) reacting the compound of Formula V with an alkoxyamine and an acid, to provide the compound of Formula VI as a mixture of the Z and E isomers: (e) isomerizing the compound of Formula VI by treatment with a strong acid and simultaneously converting to the desired acid salt of Formula VII with an enriched Z isomer, wherein the Z isomer predominates over the E-isomer by at least about a 90:10 ratio; and (f) reacting said acid salt in step (e) with a base to form a free base of the formula: wherein said free base contains an enriched Z-isomer, with the Z-isomer predominating over the E-isomer by at least about a 90:10 ratio.