Ethylenediamine → HCID 18764906, compound

HRID 480556Notes

Reaction equation

HRID 480556 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].[N:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]=O.[BH4-].[Na+]>CO>[N:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:2]=1[CH2:1][NH:4][CH:6]([NH:5][CH2:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][N:5]=1)[CH3:11]

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 142732-PyridinecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 18764906HCID 18764906, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

First N,N′-bis(pyridin-2ylmethyl)-ethanediamine (bispicen) was synthesised by the following procedure. Ethylenediamine (26 ml, 0.38 mol) was dissolved in 200 ml dry methanol. To this mixture 74 ml (0.76 mol) pyridincarboxaldehyde was added. The mixture was refluxed for 2 h, after which the mixture was left to cool to RT and in small portions 40 g of NaBH4 was added. The mixture was subsequently stirred for 16 h at RT. The methanol was evaporated and 500 ml of water was added. The aqueous mixture was extracted by three portions of dichloromethane (100 ml) and the dichloromethane solution was dried over sodium sulfate, filtered off and the solvent was removed. The dark oil containing N,N′-bis(pyridin-2ylmethyl)-ethanediamine (73.7 g; 81%) was analysed by NMR and used without further purification. 1H-nmr (CDCl3) δ 2.20 (br, NH); 2.78 (s, 4H); 3.85 (s, 4H); 7.00-7,7.40 (m, 4H); 7.58 (m, 2H); 8.45 (m, 2H).

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. waitafter which the mixture was left
  3. additionwas added
  4. customThe methanol was evaporated
  5. addition500 ml of water was added
  6. extractionThe aqueous mixture was extracted by three portions of dichloromethane (100 ml)
  7. dry with materialthe dichloromethane solution was dried over sodium sulfate
  8. filtrationfiltered off
  9. customthe solvent was removed
  10. additionThe dark oil containing N,N′-bis(pyridin-2ylmethyl)-ethanediamine (73.7 g; 81%)
  11. customused without further purification

Sources & evidence

ORD record
ord-a36885de13344fe0ab29bcb62a4c9a6a
Source dataset
uspto-grants-2003_11
Patent number
US06653271B2

Reaction notes

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