Water → Dimyristylamine

Temperature

0 °C

47 mmol of ditetradecylamide (20 g) were dissolved in 700 ml of anhydrous THF, under nitrogen, in a round-bottomed flask equipped with a condenser and a drying tube. The mixture was cooled to 0° C. and then 89 mmol of lithium aluminum hydride LiAlH4 (3.4 g) were added. After addition, the mixture was then heated under reflux for 5 hours, with vigorous stirring. Once the reaction was complete, the mixture was cooled to 0° C. in order to carry out the hydrolysis by successive addition of 3.4 ml of water, 6.8 ml of 1N sodium hydroxide and 3.4 ml of water. After stirring for 1 hour at room temperature, the crude reaction material was filtered on a Büchner funnel and the filtrate was concentrated. The product obtained was then purified on 1.5 equivalents of A-15 resin (15 g) in 300 ml of THF, with stirring for 30 minutes. The resin was filtered and redissolved in 300 ml of THF, with addition of 2 equivalents of triethylamine (19.2 ml). After stirring for 30 minutes, the solution was filtered and the filtrate was concentrated to give 17.72 g of a white solid (yield: 92%).

1. customequipped with a condenser and a drying tube
2. additionAfter addition
3. temperaturethe mixture was then heated
4. temperatureunder reflux for 5 hours, with vigorous stirring
5. temperaturethe mixture was cooled to 0° C. in order
6. customthe hydrolysis
7. customthe crude reaction material
8. filtrationwas filtered on a Büchner funnel
9. concentrationthe filtrate was concentrated
10. customThe product obtained
11. stirringwith stirring for 30 minutes
12. filtrationThe resin was filtered
13. stirringAfter stirring for 30 minutes
14. filtrationthe solution was filtered
15. concentrationthe filtrate was concentrated

ORD record

ord-dad7ca8276c04211be34ed25b2814f6c

Source dataset

uspto-grants-2004_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06812218B2