Sodium Hydroxide → 4-[[trans-2-(1-Piperidyl)cyclohexyl]oxy]benzoic acid

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 4-[[trans-2-(1-piperidyl)cyclohexyl]oxy]benzoate (Part B) (2.232 g, 7.03 mmol) and 10.6 mL (10.6 mmol) of 1.0 N NaOH in 60 mL of 1:1 mixture of MeOH/THF was stirred at 80° C. for 20 h. The mixture was then cooled to room temperature, stirred for additional 7 h, and concentrated under reduced pressure. The residue was dissolved in 50 mL of 1.0 N HCl. This solution was extracted with 200 mL of EtOAc. The organic layer was washed with 200 mL of water. The combined aqueous layers were cooled to 0° C. and neutralized with 15 mL of 2.0 N NaOH. They were then concentrated under reduced pressure and the residue was taken up in 10% MeOH in CH2Cl2 and then filtered. The filtrate was concentrated and the residue was dried over P2O5 in a vacuum oven at 55° C.

Provenance & Evidence