Triethylamine → Bicyclo [2.2.2]octane-1-carboxylic acid (4-{isopropyl-[2-(2-methoxyphenyl)ethyl]amino}butyl)amide

Participants

Reaction Conditions

Reaction Steps

Bicyclo[2.2.2]octane-1-carboxylic acid (0.53 g, 3.4 mmol), and thionyl chloride (1 ml, 13 mmol) dissolved in 10 ml toluene, were heated at 80° C. for 3 h. The solvent was partly removed and the residue added dropwise to a solution of 4-{isopropyl-[2-(2-methoxyphenyl)-ethyl]-aminobutylamine (1.2 g, 4.5 mmol) and triethylamine (3 ml, 20 mmol) in 10 ml methylene chloride at 0° C. and stirred for 1 h at room temperature. The mixture was charged on a silica gel column and eluated with hexane/ethyl acetate/triethylamine (16:4:1) to yield 1.1 g (86%) of an oil.

Provenance & Evidence