Acetic Acid → N-(3,5-bistrifluoromethylbenzyl)-N-ethylamine

HRID 604094Notes

Reaction equation

HRID 604094 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH:6]=O.[CH2:17]([NH2:19])[CH3:18].C(O)(=O)C.C(=O)(O)[O-].[Na+]>ClCCCl>[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH2:6][NH:19][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6341EthylamineHCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 516892Sodium Bicarbonate

Product 1

HCID 59735055N-(3,5-bistrifluoromethylbenzyl)-N-ethylamine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

3,5-Bis-trifluoromethylbenzaldehyde (3.00 g) is dissolved in 1,2-dichloroethane (50 ml), and thereto are added 70% aqueous ethylamine solution (0.80 ml) and acetic acid (2.1 ml), followed by an addition of triacetoxy-sodium borohydride (13.1 μg) at room temperature over 1 hour with stirring. The mixture is stirred at room temperature for additional 30 minutes, and to the reaction mixture is then added a saturated aqueous sodium bicarbonate solution, and the mixture is extracted with ethyl acetate. The organic layer is washed successively with a saturated aqueous sodium bicarbonate solution and a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane ethyl acetate=4:1) to give (3,5-bis-trifluoromethyl-benzyl)-ethyl-amine (1.52 g). MS (m/z): 272 [M+H]+

Workup

  1. stirringThe mixture is stirred at room temperature for additional 30 minutes
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe organic layer is washed successively with a saturated aqueous sodium bicarbonate solution
  4. dry with materiala saturated brine, dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography (hexane ethyl acetate=4:1)

Sources & evidence

ORD record
ord-abc0fbc415f5447cac19313227430e11
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

Loading…