Ethylenediamine → HCID 11614269, compound

HRID 1983558Notes

Reaction equation

HRID 1983558 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.[CH2:14]([NH2:17])[CH2:15][NH2:16].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[CH:13][C:4]=1[CH2:3][N:16]([CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)[CH2:15][CH2:14][N:17]([CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 11430Potassium CarbonateHCID 30838232-(Chloromethyl)quinoline hydrochloride

Product 1

HCID 11614269HCID 11614269, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-chloromethylquinoline hydrochloride (1.07 g, 5 mmol), ethylenediamine (75.0 mg 1.25 mmol), potassium carbonate (2.07 g, 15 mmol) and acetonitrile (10 mL) was refluxed by heating for 48 hours. The solvent was evaporated under reduced pressure, and then the residue was separated by phase separation using chloroform and water. The organic layer was dried, and the solvent was evaporated. The residue was washed with acetone to obtain the objective compound as white powder (0.70 g, 89%).

Workup

  1. temperaturewas refluxed
  2. temperatureby heating for 48 hours
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was separated by phase separation
  5. customThe organic layer was dried
  6. customthe solvent was evaporated
  7. washThe residue was washed with acetone

Sources & evidence

ORD record
ord-6cb07f7dfa4d42678e235870d6ec7c88
Source dataset
uspto-grants-2009_06
Patent number
US07541467B2

Reaction notes

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