Dimethylformamide → 7-[4-(2-Butoxyethoxy)phenyl]-1-crotyl-n-[4-[n-methyl-n-(tetrahydropyran-4-yl)aminomethyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide

Participants

Reaction Steps

In DMF (3.9 ml) was dissolved 7-[4-(2-butoxyethoxy)phenyl)-1-crotyl-2,3-dihydro-1-benzazepine-4-carboxylic acid (0.20 g). To the solution was added thionyl chloride (82 μl), and the mixture was stirred at room temperature for 1 hour. The solvent was removed under reduced pressure, and a solution of the resulting residue in THF was added dropwise to a solution of 4-[methyl(tetrahydropyranyl-4-yl)aminomethyl]aniline (111 mg) and triethylamine (0.31 ml) in THF (3.3 ml) under ice-cooling, and the mixture was stirred at room temperature for 2 hours. The reaction solution was added to water, and the mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the resulting residue was purified with silica gel column chromatography (ethyl acetate/ethanol=4/1), which was recrystallized from isopropyl ether/ethyl acetate to give 7-[4-(2-butoxyethoxy)phenyl]-1-crotyl-N-[4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (Compound 83) (9 mg).

Provenance & Evidence