Chloride → HCID 59564617, compound

Participants

Reaction Conditions

Reaction Steps

4-(2-Carboxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester, (0.060 g, 0.195 mmol) is dissolved in 5 mL of dry CH2Cl2 under argon. The solution is cooled to 4° C. and a 2 M solution of oxallyl chloride (0.10 mL, 0.21 mmol) is added in a drop-wise fashion resulting in gas evolution. After stirring the mixture for 30 min, 1 drop of DMF is added and the mixture is stirred at room temperature for 30 min. The reaction mixture is cooled to 4° C. and 4-trifluoromethyl-benzene-1,2-diamine (0.069 g, 0.390 mmol) and diisopropylethyl amine (0.092 mL, 0.500 mmol) are added. The reaction is warmed to room temperature and stirred for 1 h. The mixture is diluted with 50 mL EtOAc followed by 20 mL of sat. NH4Cl. The organic phase is washed with 2×20 mL of H2O and 1×20 mL of brine. The organic phase is dried with MgSO4, filtered and concentrated. The residue is applied to a SiO2 prep plate and eluted with 50% EtOAc/hexanes to give 0.045 g of 4-[2-(2-amino-4-trifluoromethyl-phenylcarbamoyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester.

Provenance & Evidence