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4-[(4-chloro-phenyl)-(3-methoxy-benzoyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester

N-(4-chloro-phenyl)-3-methoxy-N-piperidin-4-yl-benzamide

cyclohexene oxide

→

(+/−)—N-(4-chloro-phenyl)-N-[trans-1-(2-hydroxy-cyclohexyl)-piperidin-4-yl]-3-methoxy-benzamide

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실험 절차

The title compound, MS (ISP): m/e=519.4 (M+H+), white foam, was prepared as for example 98, steps (A) to (F). Step (A) was performed using 4-chloro-aniline, and yielded 4-(4-chloro-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester which was acylated to 4-[(4-chloro-phenyl)-(3-methoxy-benzoyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester in step (B). This was then deprotected to N-(4-chloro-phenyl)-3-methoxy-N-piperidin-4-yl-benzamide (C), and reacted with cyclohexene oxide to give (+/−)—N-(4-chloro-phenyl)-N-[trans-1-(2-hydroxy-cyclohexyl)-piperidin-4-yl]-3-methoxy-benzamide [step (D)]. Oxidation to (+/−)-N-(4-chloro-phenyl)-3-methoxy-N-[1-(2-oxo-cyclohexyl)-piperidin-4-yl]-benzamide in step (E) and reaction with phenyl lithium [step (F)] led to the title compound of the example.

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