1,3-Propanediamine → N-(5-trifluoromethyl-2-pyridylmethyl)trimethylenediamine

5-Trifluoromethylpicolinealdehyde (3.5 g) was added dropwise at room temperature to a solution of trimethylenediamine (7.4 g) in benzene (70 ml). After the addition, the mixture was gradually heated with stirring, and then refluxed for 2 hours while removing water that azeotroped. Benzene was distilled off under reduced pressure. The residue was dissolved in ethanol (100 ml), and sodium borohydride (0.9 g) was added little by little while the solution was stirred at 10° to 15° C. The mixture was then stirred at room temperature for 2 hours, and ethanol was distilled off at less than 30° C. Dichloromethane was added to the residue, and a portion soluble in dichloromethane was separated. Dichloromethane was distilled off under reduced pressure, and volatile materials were removed at 1 mmHg and less than 60° C. to give N-(5-trifluoromethyl-2-pyridylmethyl)trimethylenediamine (3.5 g) as a colorless oil.

1. additionAfter the addition
2. temperaturethe mixture was gradually heated
3. temperaturerefluxed for 2 hours
4. customwhile removing water
5. customthat azeotroped
6. distillationBenzene was distilled off under reduced pressure
7. dissolutionThe residue was dissolved in ethanol (100 ml)
8. additionsodium borohydride (0.9 g) was added little by little while the solution
9. stirringwas stirred at 10° to 15° C
10. stirringThe mixture was then stirred at room temperature for 2 hours
11. distillationethanol was distilled off at less than 30° C
12. additionDichloromethane was added to the residue
13. customa portion soluble in dichloromethane was separated
14. distillationDichloromethane was distilled off under reduced pressure, and volatile materials
15. customwere removed at 1 mmHg and less than 60° C.

ORD record

ord-c188263d82cb457ea80ef9543b71f9b5

Source dataset

uspto-grants-1989_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04812454