Ethylenediamine → N~1~-(Pyridin-2-yl)ethane-1,2-diamine

HRID 1883553Notes

Reaction equation

HRID 1883553 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:8][CH2:9][CH2:10][NH2:11]>>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:8][CH2:9][CH2:10][NH2:11]

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 79732-Bromopyridine

Product 1

HCID 410428N~1~-(Pyridin-2-yl)ethane-1,2-diamineYield 117.8%

Procedure

2-Bromopyridine (10.00 g, 63.3 mmol) was added dropwise to 1,2-diaminoethane (76.00 g, 126.6 mmol) under nitrogen at 20° C. with stirring. The reaction mixture was stirred at 20° C. for 4 h. and then under reflux for 24 h. The reaction mixture was concentrated in vacuo and purified by column chromatography on flash silica eluting with dichloromethane, ethanol and ammonia (30:8:1) to afford the title compound as a red oil (10.23 g). TLC SiO2, (Dichloromethane, ethanol, ammonia; 30:8:1) Rf=0.14. Mass Spectrum m/z 138 (MH+ for C6H11N3).

Workup

  1. stirringThe reaction mixture was stirred at 20° C. for 4 h.
  2. temperatureunder reflux for 24 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. custompurified by column chromatography on flash silica eluting with dichloromethane, ethanol and ammonia (30:8:1)

Sources & evidence

ORD record
ord-092f00f10aaf42d8a3e72d73b5f76f3e
Source dataset
uspto-grants-2004_07
Patent number
US06762170B1

Reaction notes

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