Potassium Carbonate → Ethyl 2-ethyl-3-[3-[4-(trifluoromethyl)benzylaminomethyl]-4-methoxyphenyl]propanoate

HRID 1826088Notes

Reaction equation

HRID 1826088 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH2:12][CH:13]([CH2:19][CH3:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].[F:27][C:28]([F:38])([F:37])[C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Br)=[CH:31][CH:30]=1>CN(C)C=O>[CH2:17]([O:16][C:14](=[O:15])[CH:13]([CH2:19][CH3:20])[CH2:12][C:6]1[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:4]([CH2:3][NH:2][CH2:33][C:32]2[CH:31]=[CH:30][C:29]([C:28]([F:27])([F:37])[F:38])=[CH:36][CH:35]=2)[CH:5]=1)[CH3:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 22139981Ethyl 2-[(3-aminomethyl-4-methoxyphenyl)-methyl]butyrate hydrochloride

Product 1

HCID 11122720Ethyl 2-ethyl-3-[3-[4-(trifluoromethyl)benzylaminomethyl]-4-methoxyphenyl]propanoateYield 32.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 3-[3-(aminomethyl)-4-methoxyphenyl]-2-ethylpropanoate hydrochloride (203 mg, 0.673 mmol) in N,N-dimethylformamide (4 mL), potassium carbonate (232 mg, 1.68 mmol) and 4-(trifluoromethyl)benzyl bromide (169 mg, 0.707 mmol) were added, and then the mixture was stirred for 3 hours at room temperature and for 4 hours under heating at 60° C. After cooling, the mixture was poured in ice water, which was extracted with diethyl ether. The organic later was washed with water and brine, dried over anhydrous sodium sulfate, and then concentrated. The residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=2:1 v/v) to afford 92.3 mg (32%) of the title compound as a colorless oil.

Workup

  1. temperatureunder heating at 60° C
  2. temperatureAfter cooling
  3. extractionwhich was extracted with diethyl ether
  4. washThe organic later was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=2:1 v/v)

Sources & evidence

ORD record
ord-4e2d6a6033d44936b638deac44b9860e
Source dataset
uspto-grants-2006_05
Patent number
US07049342B2

Reaction notes

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