4-Benzylpiperidine → 2(1H)-Quinolinone, 3,4-dihydro-1-methyl-7-(3-(4-(phenylmethyl)-1-piperidinyl)propoxy)-, ethanedioate (1:1)

Participants

Reaction Steps

4.9 Grams of 1-methyl-7-(3-chloropropoxy)-3,4-dihydrocarbostyril, 4.2 g of 4-benzylpiperidine and 3 g of triethylamine were mixed with 60 ml of dimethylformamide. The mixture was heated at 70°-80° C. for 8 hours. After the reaction was completed, the reaction mixture was concentrated under a reduced pressure to dryness. To the residue thus obtained was added 5%-sodium hydrogencarbonate aqueous solution and extracted with chloroform. The chloroform layer was washed with water and dried, then chloroform was removed by distillation. The residue thus obtained was dissolved in 30 ml of acetone, and under stirring condition a 5%-oxalic acid acetone solution was added thereto to make pH 4.5 then was allowed to stand. Precipitates thus formed were obtained by filtration, washed with acetone, then recrystallized from ethanol-ether to obtain 7.9 g (yield: 86%) of 1-methyl-7-[3-(4-benzyl-1-piperidyl)propoxy]-3,4-dihydrocarbostyril monooxalate as in the form of colorless powder. Melting point: 175°-177° C.

Provenance & Evidence