Sodium Hydroxide → HCID 13108889, compound

To a chloroform solution (200 ml) containing triethylenetetramine (60 g) was added dropwise with stirring at room temperature a chloroform solution (100 ml) containing phytyl bromide (31 g) over a period of 1 hour, and the mixture was further stirred at room temperature for 3 hours. After the completion of the dropwise addition, the reaction liquid was concentrated under reduced pressure to remove the chloroform therefrom, and the concentrate was extracted with ethyl acetate. The extract was washed with a 10% aqueous sodium hydroxide solution and saturated saline, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain a concentrate (30 g). The concentrate was dissolved in benzene (100 ml), charged with acetic anhydride (30 ml) and sodium acetate (10 g), and the resulting mixture was heated under reflux for 4 hours with stirring. After the completion of the reaction, the reaction liquid was poured in a 10% aqueous sodium hydroxide solution (300 ml) and then extracted with ethyl acetate. The extract was washed with saturated saline, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The concentrate (41 g) was treated by chromatography with an ethanol-ethyl acetate mixture over a column packed with alumina (250 g) to obtain an oily N-phytyl-N,N',N",N'"-tetraacetyltriethylenetetramine (11 g). The thus obtained N-phytyl-N,N',N",N'"-tetraacetyltriethylenetetramine (11 g) was dissolved in anhydrous tetrahydrofuran (100 ml), and thereto was added in small portions lithium aluminum hydride at room temperature with stirring. The mixture was stirred at room temperature for 1 hour and then heated under reflux with stirring for 3 hours. After cooling, the reaction liquid was charged with a 20% aqueous sodium hydroxide solution (5 ml), filtered to separate insolubles therefrom and then the filtrate was concentrated under reduced pressure. The concentrate was extracted with isopropyl ether, washed with water and saturated saline, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain as an oily product N-phytyl-N,N',N",N'"-tetraethyltriethylenetetramine (7.3 g) represented by the following formula. ##STR9## Given below are measured values of physical properties of the title compound.

1. stirringThe mixture was stirred at room temperature for 1 hour
2. temperatureheated
3. temperatureunder reflux
4. stirringwith stirring for 3 hours
5. temperatureAfter cooling
6. customthe reaction liquid
7. filtrationfiltered
8. customto separate insolubles
9. concentrationthe filtrate was concentrated under reduced pressure
10. extractionThe concentrate was extracted with isopropyl ether
11. washwashed with water and saturated saline
12. dry with materialdried over anhydrous sodium sulfate
13. concentrationconcentrated under reduced pressure

ORD record

ord-8a45855e98a14a7e96a82df61ab3a2df

Source dataset

uspto-grants-1986_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04568765