Sodium Bicarbonate → 4-(2-Aminoethyl)benzonitrile

HRID 1191039Notes

Reaction equation

HRID 1191039 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1.C([O-])(O)=O.[Na+]>>[NH2:2][CH2:3][CH2:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 516892Sodium BicarbonateHCID 457891874-(2-Aminoethyl)benzonitrile--hydrogen chloride (1/1)

Product 1

HCID 219125254-(2-Aminoethyl)benzonitrileYield 85%

Procedure

Dissolve 4-(2-amino-ethyl)-benzonitrile hydrochloride (300 mg, 1.65 mmol) into saturated aqueous NaHCO3 and extract twice with EtOAc. Dry the combined organic extracts over Na2SO4 and concentrate in vacuo to obtain 4-(2-amino-ethyl)-benzonitrile (205 mg, 85%). Dissolve 4-(2-amino-ethyl)-benzonitrile (200 mg, 1.37 mmol) in DCM (2 mL), add triethylamine (54 μL, 0.38 mmol) and cool the mixture at 0° C. Add 2,2-dimethyl-propionyl chloride (169 μL, 1.37 mmol) dropwise and allow to stir the mixture at 0° C. for 15 min and at room temperature for 2 h. Add water, separate the organic phase and extract the aqueous phase twice with DCM. Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo to obtain the desired intermediate (182 mg, 58%).

Workup

  1. extractionextract twice with EtOAc
  2. dry with materialDry the combined organic extracts over Na2SO4
  3. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-58706b225d3443df9a94b6c9389c260d
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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