Trifluoroacetic acid → 4-(2-Aminoethyl)benzonitrile

HRID 1942105Notes

Reaction equation

HRID 1942105 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11]C(=O)OC(C)(C)C)=[CH:5][CH:4]=1)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH2:11])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21955533tert-Butyl 4-cyanophenethylcarbamate

Product 1

HCID 219125254-(2-Aminoethyl)benzonitrileYield 95.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 114 (308 mg, 1.25 mmol) was dissolved in DCM (4 mL) and the solution was cooled in an ice-water bath. TFA (3.5 mL) was then added and the mixture was stirred at room temperature for 15 min. The reaction mixture was concentrated in vacuo and the residue was dissolved in EtOAc (50 mL). The solution was washed with K2CO3 (sat., 3×), brine, dried and concentrated to yield 115 (175 mg, 95%) as a pale yellow oil. MS (APCI): m/z 147 [M+H]+.

Workup

  1. temperaturethe solution was cooled in an ice-water bath
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in EtOAc (50 mL)
  4. washThe solution was washed with K2CO3 (sat., 3×), brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-20f4a97ee9bd48f3ab9b46a1167ac44a
Source dataset
uspto-grants-2013_03
Patent number
US08389529B2

Reaction notes

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