Ethylenediamine → N-((6-chloro-3-pyridinyl)methyl)-1,2-ethane-diamine

HRID 1441385Notes

Reaction equation

HRID 1441385 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([NH2:10])[CH2:8][NH2:9].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18]Cl)=[CH:14][N:13]=1>C(#N)C>[Cl:11][C:12]1[N:13]=[CH:14][C:15]([CH2:18][NH:9][CH2:8][CH2:7][NH2:10])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridine

Product 1

HCID 10997737N-((6-chloro-3-pyridinyl)methyl)-1,2-ethane-diamineYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 4.2 g (0.03 mol) of potassium carbonate and 10 ml (0.15 mol) of ethylenediamine in a 50 ml of flask placed in an ice bath, 4.8 g (0.03 mol) of 2-chloro-5-(chloromethyl)pyridine dissolved in 15 ml of acetonitrile was added dropwise and slowly for nearly 20 min. After addition, the ice bath was removed and then the mixture was stirred for 8 hours at room temperature. After the reaction was stopped, a large amount of water was added to dissolve potassium carbonate and ethylenediamine, and the mixture was extracted with dichlormethane. The lower organic phase was collected, dried, and evaporated to dryness (It was better to remove all of the ethylenediamine in the solvent since its presence would influence the following step). The obtained product was yellow oily liquid in 68% yield.

Workup

  1. additionwas added dropwise and slowly for nearly 20 min
  2. additionAfter addition
  3. customthe ice bath was removed
  4. additiona large amount of water was added
  5. dissolutionto dissolve potassium carbonate and ethylenediamine
  6. extractionthe mixture was extracted with dichlormethane
  7. customThe lower organic phase was collected
  8. customdried
  9. customevaporated to dryness (It
  10. customto remove all of the ethylenediamine in the solvent since its presence

Sources & evidence

ORD record
ord-ce7d8ff3214c4227a488308caa71f50b
Source dataset
uspto-grants-2010_02
Patent number
US07655665B2

Reaction notes

Loading…