Binap, (A+-)- → HCID 67183231, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-2-chloroanisole (3.70 g, 16.7 mmol, 1 equiv), 2,2-dimethyl-piperazine (2.2 g, 1.2 equiv) and rac-BINAP (1.04 g, 0.1 equiv) in toluene (35 mL) was degassed with compressed nitrogen for 5 min. To the mixture were added NaOt-Bu (2.3 g, 1.4 equiv) and Pd2(dba)3 (54 mg, 0.005 equiv). The resulting mixture was heated at 60° C. overnight and cooled to room temperature. EtOAc (˜200 mL) was added and the mixture was filtered through celite. The filtrate was washed with saturated aqueous K2CO3 (200 mL), saturated aqueous NaHCO3 (200 mL), and brine (200 mL) sequentially and then dried over magnesium sulfate. The resulting residue after evaporation was dissolved in EtOAc (100 mL) and treated with 2 N HCl in Et2O (100 mL) at room temperature for 2 h. A solid was collected by filtration and dried in vacuo to afford 4-(4-chloro-3-methoxy-phenyl)-3,3-dimethylpiperazine dihydrochloride (4.0 g). MS (ES) m/z 255.1 (M+H+).

Provenance & Evidence