Water → HCID 86626784, compound

HRID 604025Notes

Reaction equation

HRID 604025 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:14]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH3:15].C(=O)([O-])[O-].[K+].[K+].O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:14]([N:16]([C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH:4]=[O:5])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH3:15]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27349042-Fluoro-5-(trifluoromethyl)benzaldehydeHCID 57550990HCID 57550990, compound

Product 1

HCID 86626784HCID 86626784, compoundYield 66.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Fluoro-5-trifluoromethyl-benzaldehyde (1 g) is dissolved in toluene (5 ml) and thereto are added ethyl 7-ethylamino-heptanoate (3.98 g) and potassium carbonate (2.88 g) and the mixture is heated under reflux overnight. The reaction solution is cooled to room temperature, and thereto are added water and ethyl acetate, and the mixture is separated, and the organic layer is washed 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=97:3→83:17) to give ethyl 7-[ethyl-(2-formyl-4-trifluoromethyl-phenyl)-amino]-heptanoate (1.29 g). MS (m/z): 374 [M+H]+

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux overnight
  3. customthe mixture is separated
  4. washthe organic layer is washed with a saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=97:3→83:17)

Sources & evidence

ORD record
ord-83128758598b48778b20acf25fc9fdc8
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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