Water → 2-[(3,5-Bis-trifluoromethyl-benzyl)-ethyl-amino]-5-trifluoromethyl-benzaldehyde

HRID 604095Notes

Reaction equation

[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[CH2:6][NH:7][CH2:8][CH3:9].F[C:20]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][C:21]=1[CH:22]=[O:23].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.[Cl-].[Na+].O>[F:1][C:2]([F:17])([F:18])[C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[CH2:6][N:7]([CH2:8][CH3:9])[C:20]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][C:21]=1[CH:22]=[O:23]

Participants

Conditions

Temperature: 90 °C

Procedure

(3,5-Bis-trifluoromethyl-benzyl)-ethyl-amine (1.03 g) is dissolved in N,N-dimethylformamide (10 ml), and thereto are added 2-fluoro-5-trifluoromethyl-benzaldehyde (1.45 g) and potassium carbonate (1.48 g), and the mixture is stirred under nitrogen atmosphere at 90° C. for 3 hours and at room temperature overnight. To reaction mixture is added a saturated brine and water, and the mixture is extracted five times with ethyl acetate and the organic layer is washed twice with 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=10:1) to give 2-[(3,5-bis-trifluoromethyl-benzyl)-ethyl-amino]-5-trifluoromethyl-benzaldehyde (282 mg). MS (m/z): 444 [M+H]+

Workup

customTo reaction mixture
extractionthe mixture is extracted five times with ethyl acetate
washthe organic layer is washed twice with a saturated brine
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record: ord-634e8c16fbc34281af488f7880bc9530
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906517B2

Reaction notes

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