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

HRID 1906540Notes

Reaction equation

HRID 1906540 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-d77ba2b5b18043738d03ba4212e01ca2
Source dataset
uspto-grants-1987_03
Patent number
US04652650

Reaction notes

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