Putrescine → N-(4-aminobutyl)pyridin-2-amine

HRID 2308982Notes

Reaction equation

HRID 2308982 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][CH2:12][NH2:13]>N1C=CC=CC=1>[NH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 1045PutrescineHCID 79732-Bromopyridine

Product 1

HCID 14397369N-(4-aminobutyl)pyridin-2-amineYield 67%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Bromopyridine (10 g), 1,4-diaminobutane (35 ml) and pyridine (7 ml) were heated together under reflux for 4 hr. The excess of diaminobutane was evaporated at reduced pressure and the residue was dissolved in water. The solution was extracted with chloroform at pH 7 and then made alkaline to pH 13. The alkaline aqueous solution was extracted with more chloroform and was dried (K2CO3). The chloroform was evaporated and the residue was distilled at reduced pressure to give 2-(4-aminobutylamino)pyridine 7.0 g (67%) b.p. 136°-138° C., 2 mm Hg.

Workup

  1. temperatureunder reflux for 4 hr
  2. customThe excess of diaminobutane was evaporated at reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. extractionThe solution was extracted with chloroform at pH 7
  5. extractionThe alkaline aqueous solution was extracted with more chloroform
  6. dry with materialwas dried (K2CO3)
  7. customThe chloroform was evaporated
  8. distillationthe residue was distilled at reduced pressure

Sources & evidence

ORD record
ord-125fceb413df4aa8b92c6bd25022f578
Source dataset
uspto-grants-1987_09
Patent number
US04692456

Reaction notes

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