Cyclohexene oxide → (+/-)-N-[trans-1-(2-hydroxy-cyclohexyl)-piperidin-4-yl]-3-methoxy-N-p-tolyl-benzamide

Participants

Reaction Steps

The title compound, MS (ISP): m/e=499.0 (M+H+), was prepared as for example 141, steps (A) to (F). Step (B) was performed using 3-methoxybenzoyl chloride, and yielded 4-[(3-methoxy-benzoyl)-p-tolyl-amino]-piperidine-1-carboxylic acid tert-butyl ester. This was then deprotected to 3-methoxy-N-piperidin-4-yl-N-p-tolyl-benzamide (step C), and reacted with cyclohexene oxide to give (+/−)-N-[trans-1-(2-hydroxy-cyclohexyl)-piperidin-4-yl]-3-methoxy-N-p-tolyl-benzamide [step (D)]. Oxidation to (+/−)-3-methoxy-N-[1-(2-oxo-cyclohexyl)-piperidin-4-yl]-N-p-tolyl-benzamidein step (E) and reaction with phenyl lithium [step (F)] led to the title compound of the example.

Provenance & Evidence