1,2-Dichloroethane → HCID 69158729, compound

Participants

Reaction Steps

4-[2-(2-Carboxy-ethyl)-4-chloro-phenylamino]-piperidine-1-carboxylic acid tert-butyl ester (3.9 g, 10.1 mmol) and EDC (2.9 g, 15.3 mmol) were set stirring in CH2Cl2 (50 mL) for 2 h. The reaction mixture was dissolved in CH2Cl2 (150 mL), washed with water (2×50 mL) and brine (1×50 mL). The organic layer was dried over Na2SO4 and concentrated. The residue was purified by column chromatography (silica, 30-50% EtOAc/hexanes) to obtain 1.9 g (52%) of the desired product. TLC (silica, 50% EtOAc/hexanes): Rf=0.67. MS (electrospray): exact mass calculated for C19H25ClN2O3, 364.16. m/z found, 365.1 [M++H]. 1H NMR (400 MHz, CDCl3): 7.14-7.08 (m, 2H), 6.98 (d, J=8.61 Hz, 1H), 4.33-3.98 (m, 3H), 2.75 (t, J=7.83 Hz, 4H), 2.55-2.36 (m, 4H), 1.70-1.65 (m, 2H), 1.44 (s, 9H).

Provenance & Evidence