1,3-Propanediamine → N-(3-aminopropyl)pyridin-2-amine

HRID 2308980Notes

Reaction equation

HRID 2308980 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:8][CH2:9][CH2:10][CH2:11][NH2:12]>N1C=CC=CC=1>[NH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 4281,3-PropanediamineHCID 79732-Bromopyridine

Product 1

HCID 10606924N-(3-aminopropyl)pyridin-2-amineYield 70%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Bromopyridine (20 g), 1,3-diaminopropane (47 g) and pyridine (13 ml) were heated together under reflux for 2.5 hr. Excess of diaminopropane was evaporated at reduced pressure and the residue was dissolved in water. The pH of the solution was adjusted to pH 14 and extracted with chloroform. The extracts were dried (K2CO3), and the chloroform was evaporated. The residue was distilled at reduced pressure to give 2-(3-aminopropylamino)pyridine 13.3 g (70%) b.p. 90°-91° C., 0.02 mm Hg.

Workup

  1. temperatureunder reflux for 2.5 hr
  2. customExcess of diaminopropane was evaporated at reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. extractionextracted with chloroform
  5. dry with materialThe extracts were dried (K2CO3)
  6. customthe chloroform was evaporated
  7. distillationThe residue was distilled at reduced pressure

Sources & evidence

ORD record
ord-3e53689af15341d1899a9ba79b753a60
Source dataset
uspto-grants-1987_09
Patent number
US04692456

Reaction notes

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