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Potassium Carbonate → Methyl 2-[(4-{2-[benzyl(hexyl)amino]-2-oxoethyl}-2-methoxyphenoxy)methyl]benzoate

HRID 2111992
Notes
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Reaction equation

HRID 2111992 reaction equation
[CH2:1]([N:8]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:9](=[O:20])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([O:18][CH3:19])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][O:28][C:29](=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH2:36]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([N:8]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:9](=[O:20])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:36][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[C:29]([O:28][CH3:27])=[O:38])=[C:13]([O:18][CH3:19])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 68872097N-Benzyl-N-hexyl-2-(4-hydroxy-3-methoxyphenyl)acetamide

Product 1

HCID 68870229Methyl 2-[(4-{2-[benzyl(hexyl)amino]-2-oxoethyl}-2-methoxyphenoxy)methyl]benzoateYield 86%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

N-Benzyl-N-hexyl-2-(4-hydroxy-3-methoxyphenyl)acetamide (84 mg, 0.236 mmol), 2-bromomethylbenzoic acid methyl ester (57 mg, 0.248 mmol) and potassium carbonate anhydrous (49 mg, 0.355 mmol) were mixed in acetonitrile (5 ml). The mixture was heated to reflux overnight and then evaporated to dry. Ethyl acetate and water were added and the two phases were separated. The organic phase was washed with brine and dried (magnesium sulphate) and evaporated. Chromatography of the residue on a column (ISOLUTE® SI, 2 g/6 ml) using DCM, MeOH/DCM (0.5:99.5) as eluant gave 102 mg the desired product yield 86%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customevaporated
  4. customto dry
  5. additionEthyl acetate and water were added
  6. customthe two phases were separated
  7. washThe organic phase was washed with brine
  8. dry with materialdried (magnesium sulphate)
  9. customevaporated

Sources & evidence

ORD record
ord-be953b7e4db6404abc396560a2f614ad
Source dataset
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07521461B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes