Phosgene → HCID 15886820, compound

Participants

Reaction Steps

A solution of 1-(3-aminophenyl)-1-(4-phenylpiperazin-1-yl)-4-methyl-cyclohexane (cis isomer, 246 mg, 0.705 mmol) and triethylamine (147 μL, 1.06 mmol) in dry CH2Cl2 (15 mL) was brought to 020 C. using an ice bath. Phosgene (1.93 M in toluene, 438 μL, 0.846 mmol) was added dropwise and the resulting mixture was stirred at 020 C., under a dry N2 atmosphere, for 30 minutes. 1,4-dioxa-8-azaspiro[4.5]decane (181 μl 1.41 mmol) was added via syringe and the reaction was allowed to come to room temperature. After 2 h the reaction mixture was diluted with an equal volume of CH2Cl2, washed with H2O, dried (Na2SO4) and concentrated to give an off-white solid. The solid was washed with 30% EtOAc/hexanes to give the free base of N-[3-[4-methyl-1-(4-phenyl-1-piperazinyl)cyclohexyl]phenyl]-1,4-dioxa-8-azaspiro[4.5]decane-8-carboxamide (cis isomer) as a white solid. mp=245-247° C.

Provenance & Evidence