Cyclopentanone → N-cyclopentyl-3,4,5-trifluoroaniline

HRID 469203Notes

Reaction equation

HRID 469203 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[F:15][C:16]1[CH:17]=[C:18]([CH:20]=[C:21]([F:24])[C:22]=1[F:23])[NH2:19].[C:25]1(=O)[CH2:29][CH2:28][CH2:27][CH2:26]1.C(=O)([O-])O.[Na+]>ClC(Cl)C.C(O)(=O)C>[CH:25]1([NH:19][C:18]2[CH:17]=[C:16]([F:15])[C:22]([F:23])=[C:21]([F:24])[CH:20]=2)[CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

7

Reactant 4

HCID 8452CyclopentanoneHCID 516892Sodium BicarbonateHCID 27249913,4,5-TrifluoroanilineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 57811554N-cyclopentyl-3,4,5-trifluoroaniline

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 63651,1-DichloroethaneSolvent

Procedure

Under ice-cooling, 11.5 g of sodium triacetoxyborohydride was added in small portions to a solution of 4.0 g of 3,4,5-trifluoroaniline and 3.6 ml cyclopentanone in 150 ml dichloroethane and 3.1 ml acetic acid, and, after rising to room temperature, stirred for 3.5 hours. Aqueous saturated sodium hydrogen carbonate was added thereto, followed by extraction with chloroform and subsequent drying over anhydrous sodium sulfate. After filtration, the solvent was evaporated under a reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain 5.4 g of N-cyclopentyl-3,4,5-trifluoroaniline.

Workup

  1. temperatureUnder ice-cooling
  2. customafter rising to room temperature
  3. extractionfollowed by extraction with chloroform
  4. dry with materialsubsequent drying over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under a reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-04daa9a1e5f3408c9db0029e52590017
Source dataset
uspto-grants-2014_01
Patent number
US08629126B2

Reaction notes

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