Water → HCID 14770820, compound

Participants

Reaction Steps

A mixture of 27.60 g (79.8 mmol) 1-ethoxycarbonyl-4-(4-bromo-2,5-difluorophenyl)-1,2,3,6-tetrahydropyridine and 9.00 g (89.6 mmol) cuprous cyanide in 300 ml N,N-dimethylformamide was stirred at reflux for 20 hours. The mixture was cooled and shaken with 800 ml concentrated ammonium hydroxide, 800 ml water and 1,000 ml of dichloromethane. The organic layer was washed with water, dried (MgSO4) and evaporated. The product was purified by chromatography on silica gel and crystallization from hexane to give the title compound, mp 85°-87° C.

Provenance & Evidence