Acetic Acid → HCID 86626748, compound

HRID 603987Notes

Reaction equation

HRID 603987 reaction equation
[CH2:1]([N:3]([CH2:16][CH2:17][O:18][CH3:19])[C:4]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][C:5]=1[CH:6]=O)[CH3:2].[F:20][C:21]([F:35])([F:34])[C:22]1[CH:23]=[C:24]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:25][NH2:26].C(O)(=O)C.C(Cl)Cl>ClCCCl>[F:20][C:21]([F:34])([F:35])[C:22]1[CH:23]=[C:24]([CH:27]=[C:28]([C:30]([F:33])([F:31])[F:32])[CH:29]=1)[CH2:25][NH:26][CH2:6][C:5]1[CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=[CH:11][C:4]=1[N:3]([CH2:1][CH3:2])[CH2:16][CH2:17][O:18][CH3:19]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 5210993,5-Bis(trifluoromethyl)benzylamineHCID 86626747HCID 86626747, compound

Product 1

HCID 86626748HCID 86626748, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

2-[Ethyl-(2-methoxy-ethyl)-amino]-5-trifluoromethyl-benzaldehyde (3.7 g), 3,5-bis-trifluoromethyl-benzylamine (4.23 g), acetic acid (1.15 ml) are dissolved in 1,2-dichloroethane (30 ml), and thereto is added triacetoxy sodium borohydride (5.68 g) at room temperature and the mixture is stirred at room temperature overnight. To the reaction solution are added methylene chloride and a saturated aqueous sodium bicarbonate solution, and the mixture is separated, and the organic layer is washed with a saturated brine and the mixture is dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=19:1→4:1) to give {2-[(3,5-bis-trifluoromethyl-benzylamino)-methyl]-4-trifluoromethyl-phenyl}-ethyl-(2-methoxy-ethyl)-amine (3.38 g). MS (m/z): 503 [M+H]+.

Workup

  1. customa saturated aqueous sodium bicarbonate solution, and the mixture is separated
  2. washthe organic layer is washed with a saturated brine
  3. dry with materialthe mixture is dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=19:1→4:1)

Sources & evidence

ORD record
ord-6bf9be532c8a440295b448af147a24bb
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

Loading…