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

5-Trifluoromethylpicoline aldehyde (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 while separating water as an azeotrope, refluxed for 2 hours. Benzene was distilled off under reduced pressure, and then the residue was dissolved in ethanol (100 ml). With stirring at 10° to 15° C., sodium borohydride (0.9 g) was added little by little. The mixture was then stirred at room temperature for 2 hours. Ethanol was distilled off at less than 30° C. Dichloromethane was added to the residue, and a portion of it 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. customwhile separating water as an azeotrope
4. temperaturerefluxed for 2 hours
5. distillationBenzene was distilled off under reduced pressure
6. dissolutionthe residue was dissolved in ethanol (100 ml)
7. stirringWith stirring at 10° to 15° C.
8. additionsodium borohydride (0.9 g) was added little by little
9. stirringThe mixture was then stirred at room temperature for 2 hours
10. distillationEthanol was distilled off at less than 30° C
11. additionDichloromethane was added to the residue
12. customa portion of it soluble in dichloromethane was separated
13. distillationDichloromethane was distilled off under reduced pressure, and volatile materials
14. customwere removed at 1 mmHg and less than 60° C.

ORD-Eintrag

ord-196a48b2d40b41e897ee47e90e526120

Quelldatensatz

uspto-grants-1995_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05428032