Phenylacetaldehyde → 3-Phenyl-2-({4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}-amino)propanenitrile

HRID 2184075Notes

Reaction equation

HRID 2184075 reaction equation
[C:1]1([CH2:7][CH:8]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([C:14]#[N:15])(C)C.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1>C(Cl)Cl.O>[C:1]1([CH2:7][CH:8]([NH:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]([OH:32])([C:24]([F:25])([F:26])[F:27])[C:28]([F:29])([F:30])[F:31])=[CH:21][CH:22]=2)[C:14]#[N:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 998PhenylacetaldehydeHCID 82115Trimethylsilyl cyanideHCID 5778012-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

Product 1

HCID 224756413-Phenyl-2-({4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}-amino)propanenitrileYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of phenylacetaldehyde (0.7 mL, 5.8 mmol) and trimethylsilyl cyanide 0.8 mL, 6.0 mmol) in CH2Cl2 (2 mL) was added 2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (Oakwood, 1.6 g, 6.1 mmol). The resulting mixture was stirred at ambient temperature over 18 h. The reaction mixture was diluted with CH2Cl2 and water. The organics were washed several times with water, dried (MgSO4), and concentrated in vacuo. Purification by flash chromatography (8:1 hexanes/EtOAc) afforded the title compound as a pale yellow solid (1.4 g, 63%). MS (ES+) m/z 389 (MH+).

Workup

  1. washThe organics were washed several times with water
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customPurification by flash chromatography (8:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-98cb879f487c46668b7f0e75c9956936
Source dataset
uspto-grants-2005_05
Patent number
US06900244B2

Reaction notes

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