Ammonia → 4-(3-Methylpyridin-2-YL)butan-1-amine

HRID 370519Notes

Reaction equation

HRID 370519 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH3:7])[C:2]=1[CH3:8].[NH2-].[Na+].N.Cl.[NH2:13][CH2:14][CH2:15][CH2:16]Cl>O>[CH3:7][C:3]1[C:2]([CH2:8][CH2:16][CH2:15][CH2:14][NH2:13])=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 114202,3-LutidineHCID 24533Sodium amideHCID 114690951-Propanamine, 3-chloro-, hydrochloride

Product 1

HCID 201959674-(3-Methylpyridin-2-YL)butan-1-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,3-Lutidine (321 g) was added with stirring to a solution of sodamide (351 g) in liquid ammonia (3 1). 1-Amino-3-chloropropane hydrochloride (429g) 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 1) 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).

Workup

  1. customAny liquid ammonia lost through evaporation
  2. customAfter 2 hours the reaction was quenched by the addition of ammonium chloride (120 g)
  3. waitthe reaction mixture was left
  4. customthrough evaporation
  5. customThe residue so obtained
  6. extractionextracted with dichloromethane
  7. dry with materialThe extracts were dried (Na2SO4)
  8. customthe dichloromethane removed by evaporation
  9. distillationthe residue distilled in vacuo

Sources & evidence

ORD record
ord-a1d7435e1ff24365a8cde2d8679f4e42
Source dataset
uspto-grants-1985_07
Patent number
US04526974

Reaction notes

Loading…