Water → Methyl 4-{[{2-[(4-bromobenzyl)oxy]phenethyl}(5-ethoxy-5-oxopentyl)amino]methyl}benzoate

HRID 2110255Notes

Reaction equation

HRID 2110255 reaction equation
[Br:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][O:7][C:8]2[CH:27]=[CH:26][CH:25]=[CH:24][C:9]=2[CH2:10][CH2:11][NH:12][CH2:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.Br[CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36].C(=O)(O)[O-].[Na+].O>C(#N)C>[Br:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][O:7][C:8]2[CH:27]=[CH:26][CH:25]=[CH:24][C:9]=2[CH2:10][CH2:11][N:12]([CH2:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=2)[CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 84580Ethyl 5-bromovalerateHCID 516892Sodium BicarbonateHCID 22014995Methyl 4-({2-[2-(4-bromobenzyloxy)phenyl]ethylamino}methyl)benzoate

Product 1

HCID 22015004Methyl 4-{[{2-[(4-bromobenzyl)oxy]phenethyl}(5-ethoxy-5-oxopentyl)amino]methyl}benzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5.00 g (11.0 mmol) of methyl 4-[({2-[(4-bromobenzyl)oxy]phenethyl}amino)-methyl]benzoate from Ex. VIII, 2.30 g (11.0 mmol) of ethyl 5-bromovalerate and 1.109 g (13.21 mmol) of sodium bicarbonate in 30 ml of acetonitrile are heated at reflux for 18 hours. The reaction mixture is admixed with water and extracted with methylene chloride. The organic phase is washed with saturated sodium chloride solution and dried over magnesium sulphate and the solvent is distilled off under reduced pressure. The residue is purified by chromatography over silica gel using the mobile phase methylene chloride/methanol 100/1.

Workup

  1. temperatureat reflux for 18 hours
  2. extractionextracted with methylene chloride
  3. washThe organic phase is washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. distillationthe solvent is distilled off under reduced pressure
  6. customThe residue is purified by chromatography over silica gel using the mobile phase methylene chloride/methanol 100/1

Sources & evidence

ORD record
ord-f00837ef7c5648e8a7611d9865ee2705
Source dataset
uspto-grants-2009_04
Patent number
US07517896B2

Reaction notes

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