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Ethanol, 2-(cyclohexylamino)- → (E)-N-(4'-chlorobiphenyl-4-yl)-3-(4-{[cyclohexyl-(2-hydroxyethyl)amino]methyl}phenyl)acrylamide

HRID 735180
Notes
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Reaction equation

HRID 735180 reaction equation
[CH:1]1([NH:7][CH2:8][CH2:9][OH:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:36])/[CH:26]=[CH:27]/[C:28]3[CH:33]=[CH:32][C:31]([CH2:34]Cl)=[CH:30][CH:29]=3)=[CH:20][CH:19]=2)=[CH:14][CH:13]=1>CN(C=O)C>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[CH:20][C:21]([NH:24][C:25](=[O:36])/[CH:26]=[CH:27]/[C:28]3[CH:29]=[CH:30][C:31]([CH2:34][N:7]([CH:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)[CH2:8][CH2:9][OH:10])=[CH:32][CH:33]=3)=[CH:22][CH:23]=2)=[CH:14][CH:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 17827Ethanol, 2-(cyclohexylamino)-HCID 68816418(E)-N-(4'-chlorobiphenyl-4-yl)-3-(4-chloromethylphenyl)acrylamide

Product 1

HCID 57845786(E)-N-(4'-chlorobiphenyl-4-yl)-3-(4-{[cyclohexyl-(2-hydroxyethyl)amino]methyl}phenyl)acrylamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

0.24 g (1.7 mmol) of 2-cyclohexylaminoethanol are added to a suspension of 130 mg (0.34 mmol) of (E)-N-(4′-chlorobiphenyl-4-yl)-3-(4-chloromethylphenyl)acrylamide in 10 mL of DMF and the mixture is stirred for 48 hours at 80° C. Then the reaction mixture is poured onto water and the precipitate formed is suction filtered and washed with water. The solid is dried in the circulating air dryer at 50° C. Yield: 20 mg (10% of theory); C30H33ClN2O2 (M=489.05); melting point: 178° C.-179° C.; calc.: molecular ion peak (M+H)+: 489/491 (Cl); found: molecular ion peak (M+H)+: 489/491 (Cl).

Workup

  1. additionThen the reaction mixture is poured onto water
  2. customthe precipitate formed
  3. filtrationfiltered
  4. washwashed with water
  5. customThe solid is dried in the circulating air dryer at 50° C

Sources & evidence

ORD record
ord-835557360fcd43bf91259c895398a2d1
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07592373B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes