Yield: 91%

Reaction Conditions:

with sulfuric acid for 72 h;Reflux;

Steps:

13A
A solution of 3-(piperidin-4-yl)benzoic acid (480 mg, 2.34 mmol) and H2SO4 (0.10 mL, 1.9 mmol) in MeOH (10 mL) was stirred at reflux for 72 h. After evaporation of the solvent, the residue was taken up in 1N NaOH and extracted 3x with ethyl acetate. The combined extracts were dried over Na₂SO₄, filtered and evaporated to give methyl 3- (piperidin-4-yl)benzoate (0.47 g, 91%) as a colorless oil. MS (ESI): m/z 219.9 (M+H).

References:

BRISTOL-MYERS SQUIBB COMPANY;SMALLHEER, Joanne M.;HU, Carol Hui;VALENTE, Meriah Neissel;SHAW, Scott A.;VOKITS, Benjamin P.;HALPERN, Oz Scott WO2017/160632, 2017, A1 Location in patent:Page/Page column 87