Acetic Acid → 1-{4-[5-(3-Chloro-4-cyclohexylphenyl)-[1,2,4]-oxadiazol-3-yl]benzyl}4-methyl piperidine-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A solution of sodium hydroxide (0.1 g, 0.0023 mol) and potassium hydroxide (85% assay, 0.13 g, 0.0020 mol) in demineralized water (2 mL) is added to a solution of 4-methyl-1-{4-[5-(3-chloro-4-cyclohexylphenyl)-[1,2,4]-oxadiazol-3-yl]benzyl}piperidine-4-carboxylic acid ethyl ester (0.3 g, 0.00057 mol) in tetrahydrofuran and ethanol (14 mL, 1:1). The reaction mixture is heated under reflux (80° C.) for 2 hrs. It is then concentrated under reduced pressure to give a crude residue which is dissolved in demineralized water (10 mL) and acidified to pH˜4-5 with 20% aqueous acetic acid solution. The resultant solid is filtered, dried and washed with acetone (2×10 mL). Solid is dried under vacuum to get 1-{4-[5-(3-chloro-4-cyclohexylphenyl)-[1,2,4]-oxadiazol-3-yl]benzyl}4-methyl piperidine-4-carboxylic acid.

Provenance & Evidence