Potassium Carbonate → Methyl 4-([(5-methoxy-5-oxopentyl)[2-({4-[(E)-2-phenylethenyl]benzyl}-oxy)phenethyl]amino}methyl)benzoate

HRID 8135Notes

Reaction equation

HRID 8135 reaction equation
[OH:1][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[CH2:4][CH2:5][N:6]([CH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1)[CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12].Cl[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([CH:38]=[CH:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:34][CH:33]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:14][O:13][C:11](=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7][N:6]([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:24][CH:25]=1)[CH2:5][CH2:4][C:3]1[CH:26]=[CH:27][CH:28]=[CH:29][C:2]=1[O:1][CH2:31][C:32]1[CH:37]=[CH:36][C:35](/[CH:38]=[CH:39]/[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 35309884-ChloromethylstilbeneHCID 11304109Methyl 4-(((2-hydroxyphenethyl)(5-methoxy-5-oxopentyl)amino)methyl)benzoate

Product 1

HCID 22015012Methyl 4-([(5-methoxy-5-oxopentyl)[2-({4-[(E)-2-phenylethenyl]benzyl}-oxy)phenethyl]amino}methyl)benzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.0 g (2.50 mmol) of methyl 4-{[(2-hydroxyphenethyl)-(5-methoxy-5-oxopentyl)-amino]methyl}benzoate from Ex. 1, 0.687 g (3.00 mmol) of 4-(chloromethyl)stilbene and 0.520 g (3.75 mmol) of potassium carbonate in 10.0 ml of acetonitrile are heated at reflux for 18 hours. The solution is filtered and the solvent is distilled off under reduced pressure. The crude product is purified by chromatography over silica gel using the mobile phase cyclohexane/ethyl acetate 4/1.

Workup

  1. temperatureat reflux for 18 hours
  2. filtrationThe solution is filtered
  3. distillationthe solvent is distilled off under reduced pressure
  4. customThe crude product is purified by chromatography over silica gel using the mobile phase cyclohexane/ethyl acetate 4/1

Sources & evidence

ORD record
ord-ed15b91395d4451ea25ac2df9e79a8c9
Source dataset
uspto-grants-2006_08
Patent number
US07087644B1

Reaction notes

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