Pyridine → N-(2-methoxyphenethyl)-4-(trifluoromethyl)benzamide

HRID 445363Notes

Reaction equation

HRID 445363 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][NH2:11].N1C=CC=CC=1.[F:18][C:19]([F:30])([F:29])[C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1>O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][NH:11][C:24](=[O:25])[C:23]1[CH:27]=[CH:28][C:20]([C:19]([F:18])([F:29])[F:30])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 748962-Methoxyphenethylamine

Product 1

HCID 17429727N-(2-methoxyphenethyl)-4-(trifluoromethyl)benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 100 mL round-bottomed flask was added 2-(2-methoxyphenyl)ethylamine (1510 mg, 10 mmol, Aldrich), pyridine (10 mL), 4-(trifluoromethyl)benzoyl chloride (2 mL, 10 mmol, Fluka). The reaction mixture was stirred at RT for 1 h. The reaction mixture was diluted with water (20 mL) and extracted with EtOAc (2×50 mL). The organic extract was washed with saturated NaHCO3 (20 mL), saturated NaCl (20 mL), dried over Na2SO4, filtered and concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with 20% EtOAc/CH2Cl2 to give N-(2-methoxyphenethyl)-4-(trifluoromethyl)benzamide. MS (ESI pos. ion) m/z: 324 (M+1).

Workup

  1. extractionextracted with EtOAc (2×50 mL)
  2. extractionThe organic extract
  3. washwas washed with saturated NaHCO3 (20 mL), saturated NaCl (20 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customthe residue was purified by silica gel chromatography
  8. washeluting with 20% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-6222f316366c477c9d9909672367cb5f
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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