Sodium Carbonate → Methyl 4-[[(5-ethoxy-5-oxopentyl)[2-(2-methoxyphenyl)ethyl]amino]methyl]benzoate

HRID 2110241Notes

Reaction equation

HRID 2110241 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][CH:20]=[CH:19][C:4]=1[CH2:5][CH2:6][NH:7][CH2:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1.Br[CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH2:31]([O:30][C:28](=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24][N:7]([CH2:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1)[CH2:6][CH2:5][C:4]1[CH:19]=[CH:20][CH:21]=[CH:22][C:3]=1[O:2][CH3:1])[CH3:32]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 84580Ethyl 5-bromovalerateHCID 11231852Methyl 4-(((2-methoxyphenethyl)amino)methyl)benzoate

Product 1

HCID 22015009Methyl 4-[[(5-ethoxy-5-oxopentyl)[2-(2-methoxyphenyl)ethyl]amino]methyl]benzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

15.0 g (50.0 mmol) of methyl 4-{[(2-methoxyphenethyl)amino]methyl}benzoate from Example I.1., 11.52 g (55.0 mmol) of ethyl 5-bromovalerate and 6.37 g (106.0 mmol) of sodium carbonate are dissolved in 30 ml of acetonitrile and heated at reflux for 18 hours. After cooling, most of the solvent is distilled off under reduced pressure and the residues are mixed with water. The mixture is extracted repeatedly with ethyl acetate, the organic phases are washed with saturated sodium chloride solution and, after drying over magnesium sulphate, the solvent is removed under reduced pressure. The crude product is purified by flash chromatography over silica gel (0.04-0.063 nm) using the mobile phase cyclohexane/ethyl acetate 4/1.

Workup

  1. temperatureheated
  2. temperatureat reflux for 18 hours
  3. temperatureAfter cooling, most of the solvent
  4. distillationis distilled off under reduced pressure
  5. additionthe residues are mixed with water
  6. extractionThe mixture is extracted repeatedly with ethyl acetate
  7. washthe organic phases are washed with saturated sodium chloride solution
  8. dry with materialafter drying over magnesium sulphate
  9. customthe solvent is removed under reduced pressure
  10. customThe crude product is purified by flash chromatography over silica gel (0.04-0.063 nm)

Sources & evidence

ORD record
ord-41ad6cdba23a484e9465f0f54882b4df
Source dataset
uspto-grants-2009_04
Patent number
US07517896B2

Reaction notes

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