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

HRID 464674Notes

Reaction equation

HRID 464674 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. The mixture was stripped to remove the excess of diaminopropane and the residue taken up in water. The pH was adjusted to 14 and extracted with chloroform. The extracts were dried (K2CO3), stripped and the residue distilled at reduced pressure to give 2-(3-aminopropylamino)pyridine (13.3 g; 70%) b.p.0.02 90°-91° C.

Workup

  1. temperatureunder reflux for 2.5 hr
  2. customto remove the excess of diaminopropane
  3. extractionextracted with chloroform
  4. dry with materialThe extracts were dried (K2CO3)
  5. distillationthe residue distilled at reduced pressure

Sources & evidence

ORD record
ord-557b7ec45f324b5f8366163f44b6450b
Source dataset
uspto-grants-1985_10
Patent number
US04548940

Reaction notes

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