Potassium Carbonate → {3-[3-(2-chloro-3-trifluoromethyl-benzylamino)-propoxy]-phenyl}-acetic Acid Methyl Ester

HRID 902678Notes

Reaction equation

HRID 902678 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14]Br)[CH:6]=1.[Cl:17][C:18]1[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20][NH2:21].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][NH:21][CH2:20][C:19]2[CH:22]=[CH:23][CH:24]=[C:25]([C:26]([F:27])([F:28])[F:29])[C:18]=2[Cl:17])[CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 52242072-Chloro-3-(trifluoromethyl)benzylamineHCID 10565189Methyl [3-(3-bromopropoxy)phenyl]acetate

Product 1

HCID 69254653{3-[3-(2-chloro-3-trifluoromethyl-benzylamino)-propoxy]-phenyl}-acetic Acid Methyl EsterYield 75.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of [3-(3-bromo-propoxy)-phenyl]-acetic acid methyl ester (1.5 g, 5.26 mmol) and 2-chloro-3-trifluoromethyl-benzylamine (1 g, 4.77 mmol) in acetonitrile (300 ml) was treated with solid potassium carbonate (0.79 g, 5.74 mmol). The reaction was heated to reflux and stirred overnight. Upon cooling to room temperature, the reaction was filtered through a pad of celite, washed with EtOAc, and the filtrate was concentrated in vacuo. The crude product was purified by column chromatograph (EtOAc:Hexane/30:90) to give the title compound as an oil (1.5 g, 50%). MS m/e 402.2 (M+H)+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. filtrationthe reaction was filtered through a pad of celite
  4. washwashed with EtOAc
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe crude product was purified by column chromatograph (EtOAc:Hexane/30:90)

Sources & evidence

ORD record
ord-eeffc4fe615649d48e442c90a3331bd2
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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