Reaction #452461

Reaction equation

propane-1,3-diamine

pyridine

→

N-(pyridin-2-yl)propane-1,3-diamine

Yield 76.0%

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   TemperatureThe reaction mixture was heated
3. 3
   Temperatureat reflux for 18 h
4. 4
   Temperaturecooled
5. 5
   Otherthe volatiles evaporated in vacuo
6. 6
   workup.ADDITIONTo the residue was added tetrahydrofuran (1 l)
7. 7
   Filtrationthe precipitate was filtered off
8. 8
   Washwashed with tetrahydrofuran (0.5 l)
9. 9
   OtherThe solvent was evaporated in vacuo
10. 10
    workup.DISTILLATIONthe residue purified by distillation at 95-97° C.

Procedure

To a solution of propane-1,3-diamine (310 ml, 3.63 mol) in dry pyridine (75 ml) kept under an atmosphere of nitrogen 2-bromopyridine (70 ml, 0.73 mol) was added. The reaction mixture was heated at reflux for 18 h, cooled and the volatiles evaporated in vacuo. To the residue was added tetrahydrofuran (1 l) and the precipitate was filtered off and washed with tetrahydrofuran (0.5 l). The solvent was evaporated in vacuo and the residue purified by distillation at 95-97° C. and 2×10-2 mbar affording 83.37 g (76%) of N-(pyridin-2-yl)propane-1,3-diamine.

Source