Triethylamine → (E)-N-(4'-chlorobiphenyl-4-yl)-3-{4-[(cyclopentylmethylamino)methyl]phenyl}acrylamide

HRID 735181Notes

Reaction equation

HRID 735181 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.C(O)(=O)C.C(O)(=O)C(O)=O.[CH:37]1([CH2:42][NH2:43])[CH2:41][CH2:40][CH2:39][CH2:38]1.C(N(CC)CC)C>C1COCC1>[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:19]=[CH:20][C:21]([CH2:24][NH:43][CH2:42][CH:37]4[CH2:41][CH2:40][CH2:39][CH2:38]4)=[CH:22][CH:23]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 68816418(E)-N-(4'-chlorobiphenyl-4-yl)-3-(4-chloromethylphenyl)acrylamideHCID 68819557Cyclopentylmethylamine oxalic acid acetate

Product 1

HCID 68816079(E)-N-(4'-chlorobiphenyl-4-yl)-3-{4-[(cyclopentylmethylamino)methyl]phenyl}acrylamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A reaction mixture of 200 mg (0.523 mmol) of (E)-N-(4′-chlorobiphenyl-4-yl)-3-(4-chloromethylphenyl)acrylamide, 295 mg (1.56 mmol) of cyclopentylmethylamine oxalic acid acetate and 0.44 mL (3.12 mmol) of triethylamine in 5 mL of THF 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 (10:1)). Yield: 10 mg (4% of theory); C28H29ClN2O (M=445.0); melting point: 209° C.-210° C.; calc.: molecular ion peak (M+H)+: 445/447 (Cl); found: molecular ion peak (M+H)+: 445/447 (Cl).

Workup

  1. temperatureis 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-25dda24593b34f2688dbd2a495084710
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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