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

HRID 1193961Notes

Reaction equation

HRID 1193961 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 at 5° to 10° C. to a solution of ethylenediamine (9 g) in acetonitrile (50 ml). 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 mixture. Dichloromethane was added to the residue, and a portion soluble in dichloromethane was recovered. Dichloromethane was distilled off under reduced pressure, and 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 mixture
  3. additionDichloromethane was added to the residue
  4. customa portion soluble in dichloromethane was recovered
  5. distillationDichloromethane was distilled off under reduced pressure, and volatile materials
  6. customwere removed at 50° C.

Sources & evidence

ORD record
ord-66afb50f4da049a2986e51c5eb987cc5
Source dataset
uspto-grants-1989_03
Patent number
US04812454

Reaction notes

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