Benzylamine → (2E)-N-Benzyl-3-(3,4-dihydroxyphenyl)acrylamide

HRID 569637Notes

Reaction equation

HRID 569637 reaction equation
[C:1]([OH:13])(=O)/[CH:2]=[CH:3]/[C:4]1[CH:11]=[CH:10][C:8]([OH:9])=[C:6]([OH:7])[CH:5]=1.C1(N=C=NC2CCCCC2)CCCCC1.[CH2:29]([NH2:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O1CCCC1>[CH2:29]([NH:36][C:1](=[O:13])/[CH:2]=[CH:3]/[C:4]1[CH:11]=[CH:10][C:8]([OH:9])=[C:6]([OH:7])[CH:5]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 10868DicyclohexylcarbodiimideHCID 689043Caffeic Acid

Product 1

HCID 13644537(2E)-N-Benzyl-3-(3,4-dihydroxyphenyl)acrylamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To 5 ml of tetrahydrofuran containing 180 mg of caffeic acid were added 206 mg of dicyclohexyl carbodiimide and 107 mg of benzylamine. The mixture was stirred at 50° C. for 6 hours and then filtrated. The filtrate was concentrated and the residue obtained was recrystallized from ethyl acetate/hexane to give 100 mg of granular crystals.

Workup

  1. filtrationfiltrated
  2. concentrationThe filtrate was concentrated
  3. customthe residue obtained
  4. customwas recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-e12cb1269ee64004a28b81cd0e8f6276
Source dataset
uspto-grants-1988_03
Patent number
US04733002

Reaction notes

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