Sodium Trifluoroacetate → 5-Trifluoromethyl-2-(di-n-propylamino)indan

HRID 725926Notes

Reaction equation

HRID 725926 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([N:11]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][CH3:14])[CH2:5]2.[F:18][C:19]([F:24])([F:23])C([O-])=O.[Na+]>CN1C=CC=CC1=O.C(OCC)(=O)C.[Cu]I>[F:18][C:19]([F:24])([F:23])[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([N:11]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][CH3:14])[CH2:5]2

Participants

6

Reactant 2

HCID 517019Sodium TrifluoroacetateHCID 21221814(6-Bromo-indan-2-yl)-dipropyl-amine

Product 1

HCID 197102305-Trifluoromethyl-2-(di-n-propylamino)indan

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolventHCID 127551-Methyl-2(1H)-pyridinoneSolvent

Procedure

A solution of 5-bromo-2-(di-n-propylamino)indan (Example 11), sodium trifluoroacetate, and copper (I) iodide in N-methylpyridone is heated at 160° C. for 4 h under nitrogen (Chem Lett 1981, 1719). The reaction mixture is cooled to room temperature and diluted with ethyl acetate. The mixture is filtered through a layer of Celite pad and the filtrate is washed with water, brine, dried (MgSO4), filtered, and concentrated. The oil is purified by liquid chromatography to give the title compound as a yellow oil.

Workup

  1. filtrationThe mixture is filtered through a layer of Celite pad
  2. washthe filtrate is washed with water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe oil is purified by liquid chromatography

Sources & evidence

ORD record
ord-99091c0fa8264508863a54a7df4c6f40
Source dataset
uspto-grants-1998_01
Patent number
US05708018

Reaction notes

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