1-Heptanamine, N-ethyl- → HCID 13561098, compound

Participants

Reaction Steps

A 500 ml round bottom flask fitted with an addition funnel and a calcium sulfate drying tube was charged with 8.0 g (0.03 mol) of 4-(4-nitrophenyl)butyric acid in 180 ml of carbon tetrachloride. To this stirred solution was added 16.5 ml (0.19 mol) of oxalyl chloride dropwise. The addition funnel was removed and a condenser was fitted onto the flask. The reaction mixture was refluxed for 3 hours, cooled and the excess oxalyl chloride was evaporated under reduced pressure. Approximately 100 ml of dry diethyl ether was added to the solution which was subsequently cooled in ice. To this cooled solution was added 16.3 g (0.115 mol) of ethylheptylamine dissolved in approximately 60 ml of diethyl ether. The resulting reaction mixture was stirred at room temperature overnight and diluted with a mixture of water and diethyl ether. The aqueous phase was separated and further extracted three times with diethyl ether. The organic extracts were combined, washed with water, hydrochloric acid, water (2×), a 10% aqueous sodium carbonate solution and a saturated sodium chloride solution. The organic phase was separated, dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure to provide 12.847 g of N-ethyl-N-heptyl-4-nitrobenzenebutanamide as an oil.

Provenance & Evidence