반응 #435729

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cyclohexene oxide

benzoyl chloride

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

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

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

→

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

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실험 절차

The title compound, MS (ISP): m/e=485.4 (M+H+), was prepared as for example 98, steps (A) to (F). Step (A) was performed using 3-methoxy-aniline, and yielded 4-(3-methoxy-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester which was acylated with benzoyl chloride to 4-[benzoyl-(3-methoxy-phenyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester (B). This was then deprotected to N-(3-methoxy-phenyl)-N-piperidin-4-yl-benzamide (C), and reacted with cyclohexene oxide to gave (+/−)-N-[trans-1-(2-hydroxy-cyclohexyl)-piperidin-4-yl]-N-(3-methoxy-phenyl)-benzamide [step (D)]. Oxidation to (+/−)-N-(3-methoxy-phenyl)-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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