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

HRID 1153739Notes

Reaction equation

HRID 1153739 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>[NH2:13][CH2:14][CH2:15][CH2:16][CH2:8][C:2]1[C:3]([CH3:7])=[CH:4][CH:5]=[CH:6][N:1]=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-amineYield 62.3%

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 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 2-(4-aminobutyl)-3-methylpyridine (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-15b66eb331a44d92bdc353232d0db98e
Source dataset
uspto-grants-1984_12
Patent number
US04486434

Reaction notes

Loading…