Ethylenediamine → N-(2-cyano-5-pyridylmethyl)ethylenediamine
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
Product 1
Reagents, catalysts & solvents 1
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. 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
- additionAfter the addition
- distillationAcetonitrile and the excess of ethylenediamine were distilled off under reduced pressure from the reaction mixture
- additionDichloromethane was added to the residue
- customa portion of it soluble in dichloromethane was separated
- customVolatile materials were removed at 50° C.
Sources & evidence
- ORD record
- ord-1e5dbafdc4a546198400ae31a4fa2870
- Source dataset
- uspto-grants-1994_03
- Patent number
- US05298507
Reaction notes
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