Diethylamine → HCID 19907377, compound

Participants

Reaction Steps

To 10 ml of methanol was added 2.1 g of methyl p-(6-bromohexyl)dihydrocinnamate and 4.67 g of diethylamine, and the mixture was refluxed for 5 hours. The solvent was evaporated off under a reduced pressure, 50 ml of ethyl acetate was added to the residue, and the mixture was washed twice with 20 ml of water, dried over magnesium sulfate and evaporated under a reduced pressure, to obtain 1.73 g of methyl p-(6-diethylaminohexyl)dihydrocinnamate as a colorless oil. To 1.5 g of this oil was added 4.7 ml of 1N sodium hydroxide aqueous solution, the mixture was stirred with heating at 85° C. for 3 hours, and water was evaporated off under a reduced pressure to obtain a residue, which was then dried in the presence of phosphorus pentaoxide under a reduced pressure to obtain 1.5 g of sodium p-(6-diethylaminohexyl)dihydrocinnamate. To 20 ml of dimethylformamide were added 1.4 g of the above salt and 0.86 g of diethylaminoethylchloride, and the reaction mixture was stirred for 4 hours at 60° C. After adding 50 ml of a saturated sodium chloride aqueous solution, the reaction mixture was extracted three times with 20 ml of ethyl acetate, and the extract was washed three times with water, dried over magnesium sulfate and evaporated under a reduced pressure to obtain 1.43 g of 2-diethylaminoethyl p-(6-diethylaminohexyl)dihydrocinnamate as a residue. Next, 1 g of this compound and 6 ml of ethyl iodide were added to 7 ml of ethanol, and the mixture was refluxed for 8 hours and allowed to stand in a freezer. The resulting crystal was recovered by filtration, washed twice with 10 ml of ethanol, and dried in the presence of phosphorus pentaoxide under a reduced pressure to obtain 0.8 g of the title compound as a colorless crystal.

Provenance & Evidence