Reaction #549680

Reaction equation

1-Amino-3-chloropropane hydrochloride

2,3-Lutidine

sodamide

ammonia

→

4-(3-methyl-2-pyridyl)butylamine

Yield 62.3%

Solvents

water

Conditions

Workup

1. 1
   OtherAny liquid ammonia lost through evaporation
2. 2
   OtherAfter 2 hours the reaction was quenched by the addition of ammonium chloride (120 g)
3. 3
   workup.WAITthe reaction mixture was left
4. 4
   Otherthrough evaporation
5. 5
   OtherThe residue so obtained
6. 6
   Extractionextracted with dichloromethane
7. 7
   DryingThe extracts were dried (Na2SO4)
8. 8
   Otherthe dichloromethane removed by evaporation
9. 9
   workup.DISTILLATIONthe residue distilled in vacuo

Procedure

2,3-Lutidine (321 g) was added with stirring to a solution of sodamide (351 g) in liquid ammonia (3 l). 1-Amino-3-chloropropane hydrochloride (429 g) was added to this mixture over 8 minutes with stirring. Any liquid ammonia lost through evaporation was replaced. After 2 hours the reaction was quenched by the addition of ammonium chloride (120 g) and the reaction mixture was left to stand overnight to allow substantially complete escape of ammonia through evaporation. The residue so obtained was diluted with water (2 l) and extracted with dichloromethane. The extracts were dried (Na2SO4), the dichloromethane removed by evaporation and the residue distilled in vacuo to give 4-(3-methyl-2-pyridyl)butylamine (306.6 g).

Source