Reaktion #50506

Reaktionsgleichung

5-Trifluoromethylpicoline aldehyde

trimethylenediamine

→

N-(5-trifluoromethyl-2-pyridylmethyl)trimethylenediamine

Ausbeute 75.1%

Lösungsmittel

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Temperaturthe mixture was gradually heated
3. 3
   Sonstigewhile separating water as an azeotrope
4. 4
   Temperaturrefluxed for 2 hours
5. 5
   workup.DISTILLATIONBenzene was distilled off under reduced pressure
6. 6
   workup.DISSOLUTIONthe residue was dissolved in ethanol (100 ml)
7. 7
   workup.STIRRINGWith stirring at 10° to 15° C.
8. 8
   workup.ADDITIONsodium borohydride (0.9 g) was added little by little
9. 9
   workup.STIRRINGThe mixture was then stirred at room temperature for 2 hours
10. 10
    workup.DISTILLATIONEthanol was distilled off at less than 30° C
11. 11
    workup.ADDITIONDichloromethane was added to the residue
12. 12
    Sonstigea portion of it soluble in dichloromethane was separated
13. 13
    workup.DISTILLATIONDichloromethane was distilled off under reduced pressure, and volatile materials
14. 14
    Sonstigewere removed at 1 mmHg and less than 60° C.

Vorschrift

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.

Quelle