3-(Benzyl(3-fluorophenyl)amino)-1,1,1-trifluoropropan-2-ol → 3-[(3-Fluorophenyl)amino]-1,1,1-trifluoro-2-propanol

HRID 990562Notes

Reaction equation

HRID 990562 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8](CC2C=CC=CC=2)[CH2:9][CH:10]([OH:15])[C:11]([F:14])([F:13])[F:12])[CH:5]=[CH:6][CH:7]=1>CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([NH:8][CH2:9][CH:10]([OH:15])[C:11]([F:13])([F:12])[F:14])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 108051203-(Benzyl(3-fluorophenyl)amino)-1,1,1-trifluoropropan-2-ol

Product 1

HCID 111387333-[(3-Fluorophenyl)amino]-1,1,1-trifluoro-2-propanolYield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-[(3-fluorophenyl)[phenylmethyl]amino]-1,1,1-trifluoro-2-propanol (2.56 g, 8.2 mmol) was dissolved in methanol (30 mL) and hydrogenated over 5% palladium on charcoal for 3 h. The mixture was filtered through celite, and the solvent was removed in vacuo to give 1.8 g (98%) of the desired 3-[(3-fluorophenyl)amino]-1,1,1-trifluoro-2-propanol product as an oil, 99% pure by HPLC analysis. MS m/z=224 [M+H]+.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-dfeef3abc29e41f2bb1e3741a94cc0db
Source dataset
uspto-grants-2002_10
Patent number
US06458852B1

Reaction notes

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