Cyclohexylamine → (E)-N-(4'-chlorobiphenyl-4-yl)-3-(4-cyclohexylaminomethylphenyl)acrylamide

HRID 735177Notes

Reaction equation

HRID 735177 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:33])/[CH:23]=[CH:24]/[C:25]3[CH:30]=[CH:29][C:28]([CH2:31]Cl)=[CH:27][CH:26]=3)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1>C1COCC1>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:33])/[CH:23]=[CH:24]/[C:25]3[CH:30]=[CH:29][C:28]([CH2:31][NH:7][CH:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)=[CH:27][CH:26]=3)=[CH:17][CH:16]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 68816418(E)-N-(4'-chlorobiphenyl-4-yl)-3-(4-chloromethylphenyl)acrylamide

Product 1

HCID 57845782(E)-N-(4'-chlorobiphenyl-4-yl)-3-(4-cyclohexylaminomethylphenyl)acrylamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.082 mL (0.72 mmol) of cyclohexylamine is added to a suspension of 150 mg (0.39 mmol) of (E)-N-(4′-chlorobiphenyl-4-yl)-3-(4-chloromethylphenyl)acrylamide in 5 mL of THF and the mixture is refluxed for 18 hours. Then the reaction mixture is poured onto water and the precipitate formed is suction filtered. Further purification is carried out by column chromatography on silica gel (eluant: dichloromethane/methanol (95:5 to 50:50)). Yield: 70 mg (40% of theory); C28H29ClN2O (M=444.99); melting point: 247° C.-248° C.; Calc.: molecular ion peak (M+H)+: 445/447 (Cl); found: molecular ion peak (M+H)+: 445/447 (Cl).

Workup

  1. temperaturethe mixture is refluxed for 18 hours
  2. additionThen the reaction mixture is poured onto water
  3. customthe precipitate formed
  4. filtrationfiltered
  5. customFurther purification

Sources & evidence

ORD record
ord-140ec22b74674540a4fdfacfcd1949e5
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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