Ethylenediamine → N-(2-cyano-5-pyridylmethyl)ethylenediamine

HRID 377004Notes

Reaction equation

HRID 377004 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9]Cl)=[CH:5][N:4]=1)#[N:2].[CH2:11]([NH2:14])[CH2:12][NH2:13]>C(#N)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:13][CH2:12][CH2:11][NH2:14])=[CH:5][N:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 144051235-(Chloromethyl)pyridine-2-carbonitrile

Product 1

HCID 13933560N-(2-cyano-5-pyridylmethyl)ethylenediamineYield 84.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 2-cyano-5-pyridylmethyl chloride (4.6 g) in acetonitrile (20 ml) was added dropwise to a solution of ethylenediamine (9 g) in acetonitrile (50 ml) at 5 to 10° C. After the addition, the mixture was stirred at room temperature for 3 hours. Acetonitrile and the excess of ethylenediamine were distilled off under reduced pressure from the reaction mixture. Dichloromethane was added to the residue, and a portion of it soluble in dichloromethane was separated. Dichloromethane was distilled off under reduced pressure. Volatile materials were removed at 50° C. and 1 mmHg to give N-(2-cyano-5-pyridylmethyl) ethylenediamine (4.5 g) as a colorless oil.

Workup

  1. additionAfter the addition
  2. distillationAcetonitrile and the excess of ethylenediamine were distilled off under reduced pressure from the reaction mixture
  3. additionDichloromethane was added to the residue
  4. customa portion of it soluble in dichloromethane was separated
  5. distillationDichloromethane was distilled off under reduced pressure
  6. customVolatile materials were removed at 50° C.

Sources & evidence

ORD record
ord-9d1f4ee02b2f422a98c4d5f8e82b1855
Source dataset
uspto-grants-2000_02
Patent number
US06022967

Reaction notes

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