Benzoic acid, 4-fluoro-, ethyl ester → 4-Benzylbenzoate piperidine 4-ethyl benzoate

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Reaction Steps

A mixture of 4-piperazin-1-yl-benzoic acid benzyl ester (500 mg, 1.68 mmol), 4-fluoro benzoic acid ethyl ester (1.4 g, 8.4 mmol), diisopropylethyl amine (1.47 mL, 8.4 mmol) and a catalytic amount of DMAP in DMSO (6 mL) was stirred at 130° C. in a sealed tube for 70 h. The mixture was the cooled partitioned between EtOAc and water. The EtOAc layer was collected, dried over Na2SO4, filtered and concentrated. The residue was suspended in hexanes and the suspension was then filtered. The solid obtained passed through a plug of silica gel using 0-100% EtOAc in hexanes to afford the product (480 mg, Yield; 64%). HRMS m/z calcd for C27H28N2O4 [M+H]+: 445.2122; Found: 445.2120.

Provenance & Evidence