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

HRID 231190Notes

Reaction equation

HRID 231190 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-6034632206694cfd9747fb6ab308f0f5
Source dataset
uspto-grants-1989_07
Patent number
US04845106

Reaction notes

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