Triethylsilyldiazomethane → HCID 58425624, compound

Participants

Reaction Steps

A solution of 2-(benzylamino)-4-(4-benzoylpiperazin-1-yl)benzoic acid (100 mg, 0.24 mmol) in 15 ml DCM was cooled to 0° C. under argon atmosphere, followed by the addition of triethylsilyldiazomethane (0.12 ml, 0.24 mmol). The run was quenched with 1 ml water and all the solvents were evaporated under vacuum. Methyl 2-(benzylamino)-4-(4-benzoylpiperazin-1-yl)benzoate (30 mg, 30%) was obtained by flash column chromatograph (50% ethyl acetate in hexanes), and its hydrochloride was made by bubbling HCL gas in ether solution. 1H NMR (500 MHz, DMSO-d6) δ (ppm) 3.31-3.68 (m, br, 11H), 4.42 (s, 2H), 6.06 (d, J=1.8 Hz, 1H), 6.25 (dd, J=1.8, 9.1 Hz, 1H), 7.26-7.48 (m, 10H), 7.64 (d, J=9.1 Hz, 1H), 8.06 (s, 3H). 13C NMR (125 MHz, DMSO-d6): δ (ppm) 46.1, 51.0, 95.3, 100.4, 102.8, 127.0, 127.4, 128.4, 128.5, 129.6, 132.4, 135.7, 139.3, 151.7, 154.6, 167.8, 169.1.

Provenance & Evidence