Trifluoroacetic acid → 4-(2-Phenylethyl)aniline

HRID 2299909Notes

Reaction equation

HRID 2299909 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:14]([C:11]1[CH:10]=[CH:9][C:8]([NH2:7])=[CH:13][CH:12]=1)[CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54000670HCID 54000670, compound

Product 1

HCID 830544-(2-Phenylethyl)anilineYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4-Phenethyl-phenyl)-carbamic acid tert-butyl ester (Ii, 0.90 g, 3.03 mmol) was dissolved in CH2Cl2 (15 mL) and treated with TFA (15 mL). The reaction was stirred for 20 minutes, concentrated, diluted with EtOAc (200 mL), washed twice with saturated sodium bicarbonate solution and once with brine, dried over Na2SO4, and concentrated to give 0.56 g (94%) of the desired product.

Workup

  1. concentrationconcentrated
  2. additiondiluted with EtOAc (200 mL)
  3. washwashed twice with saturated sodium bicarbonate solution and once with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-605796e07684469b91450ac4a15eecab
Source dataset
uspto-grants-2002_12
Patent number
US06495715B2

Reaction notes

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