Ethylenediamine → (2-Aminoethyl)[5-(trifluoromethyl)(2-pyridyl)]amine

HRID 31751

Reaction equation

HRID 31751 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.[CH2:12]([NH2:15])[CH2:13][NH2:14]>>[NH2:14][CH2:13][CH2:12][NH:15][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 923422-Chloro-5-(trifluoromethyl)pyridine

Product 1

HCID 2779424(2-Aminoethyl)[5-(trifluoromethyl)(2-pyridyl)]amine

Procedure

2-Chloro-5-(trifluoromethyl)pyridine (5.0 g) was heated with ethylenediamine (20 ml) at 120° C. overnight. The excess ethylenediamine was removed by rotary evaporation and the residue was partitioned between dichloromethane and 2.5 M aqueous sodium hydroxide. The aqueous layer was extracted 5 times further with dichloromethane. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried, then concentrated in vacuo to give (2-aminoethyl)[5-(trifluoromethyl)(2-pyridyl)]amine as an orange oil.

Workup

  1. customThe excess ethylenediamine was removed by rotary evaporation
  2. customthe residue was partitioned between dichloromethane and 2.5 M aqueous sodium hydroxide
  3. extractionThe aqueous layer was extracted 5 times further with dichloromethane
  4. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c90571fea176455db5acc4975a90b2f6
Source dataset
uspto-grants-2008_09
Patent number
US07425557B2

Linked notes

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