Ethylenediamine → 4-(2-Aminoethyl)benzonitrile

HRID 1698777Notes

Reaction equation

HRID 1698777 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH2:10](N)[CH2:11][NH2:12]>>[NH2:12][CH2:11][CH2:10][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 145174-Fluorobenzonitrile

Product 1

HCID 219125254-(2-Aminoethyl)benzonitrile

Procedure

4-Fluorobenzonitrile is reacted with an excess of ethylenediamine in an aprotic solvent to give 4-(2-aminoethyl)benzonitrile, which is then mono-alkylated with ethyl bromoacetate in a polar solvent such as ethanol or acetonitrile, in the presence of an inorganic base or a tertiary amine. An acylation with chloroacetyl chloride followed by a cyclization and a hydrolysis give the acid (1).

Sources & evidence

ORD record
ord-bd58d6e0eff640daa9fa9a1b13f1a28f
Source dataset
uspto-grants-2002_02
Patent number
US06344456B1

Reaction notes

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