Potassium Carbonate → HCID 68868645, compound

HRID 2111978Notes

Reaction equation

HRID 2111978 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]([CH3:25])[C:14](=[O:24])[CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:26][O:27][C:28](=[O:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:35]Br.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]([CH3:25])[C:14](=[O:24])[CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:35][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[C:28]([O:27][CH3:26])=[O:37])=[CH:19][CH:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 68871500HCID 68871500, compound

Product 1

HCID 68868645HCID 68868645, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-[2-(3,4-dimethoxyphenyl)ethyl]-3-(4-hydroxyphenyl)-N-methylpropanamide (198 mg, 0.577 mmol), 2-bromomethyl-benzoic acid methyl ester (139 mg, 0.605 mmol) and potassium carbonate, anhydrous (120 mg, 0.864 mmol) were mixed in acetonitrile (15 ml). The mixture was heated to reflux overnight and then evaporated to dry. Water and ethyl acetate were added and the two phases were separated. The organic phase was dried (magnesium sulphate) and evaporated. Chromatography of the residue on a column (ISOLUTE® SI, 2 g/6 ml) using heptane/DCM (50:50), then DCM and then MeOH/DCM (0.5:99.5) as eluant gave 172 mg the desired product, yield 61%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customevaporated
  4. customto dry
  5. additionWater and ethyl acetate were added
  6. customthe two phases were separated
  7. dry with materialThe organic phase was dried (magnesium sulphate)
  8. customevaporated

Sources & evidence

ORD record
ord-7cad2d1a387d4ca1b3cdf97119a560a5
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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