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

HRID 1274845Notes

Reaction equation

HRID 1274845 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][NH2:4].[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>>[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:4][CH2:3][CH2:2][CH2:1][NH2:5]

Participants

3

Reactant 2

HCID 4281,3-PropanediamineHCID 1049Pyridine

Product 1

HCID 10606924N-(3-aminopropyl)pyridin-2-amineYield 76%

Procedure

To a solution of propane-1,3-diamine (310 ml, 3.63 mol) in dry pyridine (75 ml) kept under an atmosphere of nitrogen 2-bromopyridine (70 ml, 0.73 mol) was added. The reaction mixture was heated at reflux for 18 h, cooled and the volatiles evaporated in vacuo. To the residue was added tetrahydrofuran (1 l) and the precipitate was filtered off and washed with tetrahydrofuran (0.5 l). The solvent was evaporated in vacuo and the residue purified by distillation at 95-97° C. and 2×10-2 mbar affording 83.37 g (76%) of N-(pyridin-2-yl)propane-1,3-diamine.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 18 h
  4. temperaturecooled
  5. customthe volatiles evaporated in vacuo
  6. additionTo the residue was added tetrahydrofuran (1 l)
  7. filtrationthe precipitate was filtered off
  8. washwashed with tetrahydrofuran (0.5 l)
  9. customThe solvent was evaporated in vacuo
  10. distillationthe residue purified by distillation at 95-97° C.

Sources & evidence

ORD record
ord-e34f485734e34352ad83a99dac7a0424
Source dataset
uspto-grants-2000_12
Patent number
US06159941

Reaction notes

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