Water → 2-(4-(5-Trifluoromethyl-2-pyridinyloxy)phenyl)ethylamine

HRID 1728317Notes

Reaction equation

HRID 1728317 reaction equation
[H-].[Na+].[NH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.Cl[C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][N:15]=1.O>CN(C=O)C>[F:21][C:20]([F:23])([F:22])[C:17]1[CH:18]=[CH:19][C:14]([O:12][C:9]2[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][NH2:3])=[CH:7][CH:8]=2)=[N:15][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5610TyramineHCID 24758Sodium hydrideHCID 923422-Chloro-5-(trifluoromethyl)pyridine

Product 1

HCID 167707892-(4-(5-Trifluoromethyl-2-pyridinyloxy)phenyl)ethylamineYield 85.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (0.78 g, 0.033 mol) was slurried in dry DMF (50 mL) and tyramine (4.31 g, 0.031 mol) added. The mixture was stirred at room temperature until effervescence ceased. A solution of 2-chloro-5-trifluoromethylpyridine (6.0 g, 0.033 mol) in DMF (10 mL) was then added. The mixture was heated at 50° C. for three hours and poured into water. This was extracted with ethyl acetate and the organic phase washed with water and dried over anhydrous sodium sulphate. Evaporation of the solvent under reduced pressure and purification of the product by column chromatography gave 7.5 g of product as an oil.

Workup

  1. temperatureThe mixture was heated at 50° C. for three hours
  2. extractionThis was extracted with ethyl acetate
  3. washthe organic phase washed with water
  4. dry with materialdried over anhydrous sodium sulphate
  5. customEvaporation of the solvent
  6. customunder reduced pressure and purification of the product by column chromatography

Sources & evidence

ORD record
ord-dab9166876fb4ce7b363b7b1a884e74d
Source dataset
uspto-grants-1994_07
Patent number
US05326766

Reaction notes

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