2-Bromopyridine → HCID 20186610, compound

HRID 2308986Notes

Reaction equation

HRID 2308986 reaction equation
[H-].[Na+].[NH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1.Br[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1>C1(C)C=CC=CC=1>[N:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[N:7]([CH2:6][CH2:5][CH2:4][NH2:3])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 79732-BromopyridineHCID 24758Sodium hydrideHCID 10606924N-(3-aminopropyl)pyridin-2-amine

Product 1

HCID 20186610HCID 20186610, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of sodium hydride (0.92 g) and 2-(3aminopropylamino)pyridine (5 g) in toluene (100 ml) was heated under nitrogen to 90° C. until initial reaction ceased, and then under reflux for 2 hr. After cooling, 2-bromopyridine (5.53 g) was added and the mixture heated under reflux for 10 hr. The mixture was poured on to ice/water (100 ml), extracted at pH 14 with chloroform, and these extracts washed with 2N HCl. The acidic aqueous solution was adjusted to pH 9 and extracted with ether and the extracts were discarded. The aqueous phase was adjusted to pH 14 and extracted with ether and the latter ethereal extracts were washed with water, dried (K2CO3) and concentrated to give 3-(N,N-dipyrid-2-ylamino)propylamine (2.93 g, 39%) as an oil which was used without further purification.

Workup

  1. customreaction
  2. temperatureunder reflux for 2 hr
  3. temperatureAfter cooling
  4. temperaturethe mixture heated
  5. temperatureunder reflux for 10 hr
  6. extractionextracted at pH 14 with chloroform
  7. washthese extracts washed with 2N HCl
  8. extractionextracted with ether
  9. extractionextracted with ether
  10. washthe latter ethereal extracts were washed with water
  11. dry with materialdried (K2CO3)
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-bf722c95e0094201b307504e41637aff
Source dataset
uspto-grants-1987_09
Patent number
US04692456

Reaction notes

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