Potassium Carbonate → (E)-N-(4'-chlorobiphenyl-4-yl)-3-(4-cyclopropylaminomethylphenyl)acrylamide

HRID 735174Notes

Reaction equation

HRID 735174 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:26])/[CH:16]=[CH:17]/[C:18]3[CH:23]=[CH:22][C:21]([CH2:24]Cl)=[CH:20][CH:19]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.CO[CH2:29][CH2:30][NH:31]C.[C:33](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][C:15](=[O:26])/[CH:16]=[CH:17]/[C:18]3[CH:19]=[CH:20][C:21]([CH2:24][NH:31][CH:30]4[CH2:33][CH2:29]4)=[CH:22][CH:23]=3)=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 300977(2-Methoxyethyl)(methyl)amineHCID 68816418(E)-N-(4'-chlorobiphenyl-4-yl)-3-(4-chloromethylphenyl)acrylamide

Product 1

HCID 68819105(E)-N-(4'-chlorobiphenyl-4-yl)-3-(4-cyclopropylaminomethylphenyl)acrylamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A reaction mixture of 100 mg (0.26 mmol) of (E)-N-(4′-chlorobiphenyl-4-yl)-3-(4-chloromethylphenyl)acrylamide, 70 mg (0.77 mmol) of 2-methoxyethylmethylamine, and 140 mg (1 mmol) of potassium carbonate in 10 mL of acetone is agitated for 24 hours at reflux temperature. The reaction mixture is evaporated down. The residue is purified by column chromatography on silica gel (eluant: dichloromethane/ethanol/ammonia (20/1/0.1)). Yield: 92 mg (81% of theory); melting point: 222° C.-223° C.; C26H27ClN2O2 (M=434.96); calc.: molecular ion peak (M+H)+: 435/37(Cl); found: molecular ion peak (M+H)+: 435/37(Cl); Rf value: 0.4 (silica gel, dichloromethane/methanol/ammonia (20:1:0.1)).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture is evaporated down
  3. customThe residue is purified by column chromatography on silica gel (eluant: dichloromethane/ethanol/ammonia (20/1/0.1))

Sources & evidence

ORD record
ord-57d855621d574912956a8b144a671465
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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