Nitrogen → 4-(2-Aminoethyl)benzonitrile

HRID 1071962Notes

Reaction equation

HRID 1071962 reaction equation
[C:1](#[N:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:9]#N.[CH3:11][CH2:12]O.CCOC(C)=O>[Pd]>[NH2:9][CH2:12][CH2:11][C:5]1[CH:6]=[CH:7][C:2]([C:1]#[N:8])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 7505BenzonitrileHCID 21584252Ethanol ethylacetate

Product 1

HCID 219125254-(2-Aminoethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
0 °C

Procedure

A solution of 4-2-azidoethyl)benzonitrile (500 mg, 2.90 mmol) in 1:1 EtOH/EtOAc (3 mL) at 0° C. was purged with N2. Then Pd/C (440 mg) was added and a H2 balloon was placed over the reaction. After stirring at 0° C. for two hours, the reaction mixture was filtered through a pad of celite and concentrated to give 4-(2-aminoethyl)benzonitrile, which was used without further purification. LCMS (ES) 147.3 m/z (M+H)+.

Workup

  1. customa H2 balloon was placed over the reaction
  2. filtrationthe reaction mixture was filtered through a pad of celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8e49e2d21a98441d9c9c80be087831c6
Source dataset
uspto-grants-2005_06
Patent number
US06908921B2

Reaction notes

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