Phosgene → HCID 9917229, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(3-aminophenyl)-1-(4-phenylpiperazin-1-yl)-4-methyl-cyclohexane (cis isomer, 90 mg, 0.258 mmol) and triethylamine (90 μL, 0.65 mmol) in dry CH2Cl2 (7 mL) was brought to 0° C. using an ice bath. Phosgene (1.93 M in toluene, 160 μL) was added dropwise and the resulting mixture was stirred at 0° C., under a dry N2 atmosphere, for 30 minutes. 3-aminoquinoline (45 mg, 0.310 mmol) was added as a solid and the reaction was allowed to come to room temperature. Upon completion of the reaction (disappearance of 3-aminoquinoline) the mixture was diluted with an equal volume of CH2Cl2, washed with H2O, dried (Na2SO4) and concentrated to give the crude urea. Silica gel chromatography yielded pure N-[3-[4-methyl-1-(4-phenyl-1-piperazinyl)cyclohexyl]phenyl]-N'-3-quinolinyl-urea (cis isomer) as an off-white solid. The HCl salt was prepared by adding excess saturated EtOAc/HCl solution to the free base in dry MeOH. Concentration of the homogeneous solution yielded a solid which was washed with EtOAc. mp=180-181° C.

Provenance & Evidence