Reaction #452467

Reaction equation

propane-1,3-diamine

tetrahydrofuran

pyridine

→

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

Yield 82.0%

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   TemperatureThe reaction mixture was heated
3. 3
   Temperatureat reflux temperature for 18 h
4. 4
   OtherTo the cooled reaction mixture
5. 5
   Filtrationthe precipitate was filtered off
6. 6
   Washwashed with tetrahydrofuran (2×50 ml)
7. 7
   OtherThe solvent was evaporated in vacuo
8. 8
   workup.DISTILLATIONthe residue purified by distillation at 154° C.

Procedure

To a solution of propane-1,3-diamine (65.1 ml, 0.764 mol) in dry pyridine (25 ml) kept under an atmosphere of nitrogen 2-chloro-quinoline (25 g, 0.153 mol) was added. The reaction mixture was heated at reflux temperature for 18 h. To the cooled reaction mixture was added tetrahydrofuran (100 ml) and the precipitate was filtered off and washed with tetrahydrofuran (2×50 ml). The solvent was evaporated in vacuo and the residue purified by distillation at 154° C. and 2.5×10-2 mbar affording 25.34 g (82%) of N-(quinolin-2-yl)propane-1,3-diamine as a crystallising oil.

Source