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

HRID 1057467Notes

Reaction equation

HRID 1057467 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([NH2:12])[CH2:9][CH2:10][NH2:11]>N1C=CC=CC=1>[NH2:11][CH2:10][CH2:9][CH2:8][NH:12][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 4281,3-PropanediamineHCID 97462-Fluoropyridine

Product 1

HCID 10606924N-(3-aminopropyl)pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirring solution of 2-fluoropyridine in pyridine (0.5 M) was added 1,3-propanediamine (5 eq), and the solution was refluxed overnight. The solution was then concentrated in vacuo and the residue was partitioned between ethyl acetate and 10% sodium carbonate. The phases were separated, and the organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed (silica; 10:1:1 EtOH/NH4OH/H2O) to afford a viscous pale yellow oil. EI-MS m/z 152 (M+H)+

Workup

  1. temperaturethe solution was refluxed overnight
  2. concentrationThe solution was then concentrated in vacuo
  3. customthe residue was partitioned between ethyl acetate and 10% sodium carbonate
  4. customThe phases were separated
  5. washthe organic phase was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed (silica; 10:1:1 EtOH/NH4OH/H2O)
  10. customto afford a viscous pale yellow oil

Sources & evidence

ORD record
ord-dca731660787477eaef9741f56729ae0
Source dataset
uspto-grants-2003_02
Patent number
US06514964B1

Reaction notes

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