N-Ethyl-1-heptanamine

14202-55-2

66793-76-8

1. n-Heptylamine (10.31 g, 89.4 mmol) was dissolved in 100 mL of dichloromethane in an ice bath. 2. pyridine (7.5 mL, 92.7 mmol) was added to the solution. 3. Acetyl chloride (8.0 mL, 11 mmol) was added slowly and dropwise over 2 minutes. 4. Remove the ice bath and allow the reaction mixture to warm naturally to room temperature and continue the reaction for 1 hour. 5. Upon completion of the reaction, the organic layer was separated by adding 100 mL of water. 6. Extract the aqueous layer with 100 mL of dichloromethane and combine the organic phases. 7. The combined organic phases were washed sequentially with 10% aqueous hydrochloric acid solution, saturated sodium bicarbonate solution and saturated sodium chloride solution. 8. 8. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain n-heptyl acetamide as a colorless liquid (13.73 g, 98% yield). 9. n-Heptylacetamide (6.076 g, 38.63 mmol) was dissolved in 6 mL of diethyl ether and slowly added dropwise to 150 mL of ether with lithium aluminum hydride (4.60 g, 0.121 mol) suspended. 10. The reaction mixture was refluxed for 8 hours and then cooled in an ice bath. 11. The reaction was quenched sequentially with 4 mL of water, 4 mL of 2 M sodium hydroxide solution and 12 mL of water. 12. The resulting suspension was filtered and the filtrate was dried with anhydrous sodium sulfate. 13. Evaporate the solvent under pressure to obtain N-ethylheptylamine as a colorless liquid (5.29 g, 95% yield).