2-Chloro-1-methylpyridinium iodide → HCID 54059442, compound

Participants

Reaction Steps

To a stirred suspension of 19.6 parts of 2-[(ethoxycarbonyl)amino]-5-(phenylmethoxy)benzoic acid in 520 parts of dichloromethane were added 12.6 parts of N,N-diethylethanamine and the whole was stirred for 5 minutes. 15.9 Parts of 2-chloro-1-methylpyridinium iodide were added and stirring was continued for 90 minutes. A solution of 18.2 parts of 4-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]-1-piperidineethanamine in 390 parts of dichloromethane was added dropwise to the whole. Upon completion, stirring was continued for 2.50 hours at room temperature. 150 Parts of water were added to the reaction mixture. The organic layer was separated, washed with a sodium hydrogen carbonate solution 10%, dried, filtered and evaporated. The oily residue was purified by HPLC over silica gel using a mixture of methylbenzene and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 24.7 parts (67%) of ethyl [2-[[2-[4[ 2-(4-fluorophenyl)-1,3-dioxolan-2-yl]-1-piperidinyl]ethyl]aminocarbonyl]-4-(phenylmethoxy)phenyl]carbamate as a residue (25).

Provenance & Evidence