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レコード

ord-a1dde79a25514dcd91f86fa875231fea

出典データセット

uspto-grants-2000_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06022967