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Homoveratrylamine → N-[2-(3,4-Dimethoxy-phenyl)-ethyl]-3-(3-methoxy-phenyl)-propionamide

HRID 2414814
Notes
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Reaction equation

HRID 2414814 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]([OH:13])=O)[CH:6]=[CH:7][CH:8]=1.Cl.C(N=C=N)C.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH2:30][CH2:31][NH2:32])[CH:25]=[CH:26][C:27]=1[O:28][CH3:29].CCOC(C)=O>C1COCC1>[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH2:30][CH2:31][NH:32][C:11](=[O:13])[CH2:10][CH2:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:25]=[CH:26][C:27]=1[O:28][CH3:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8421HomoveratrylamineHCID 8857Ethyl AcetateHCID 663363-(m-Methoxyphenyl)propionic acidHCID 21883477Ethylcarbodiimide hydrochloride

Product 1

HCID 22643372N-[2-(3,4-Dimethoxy-phenyl)-ethyl]-3-(3-methoxy-phenyl)-propionamide

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a suspension of 3-(3-methoxy-phenyl)-propionic acid (1.19 g, 6.62 mmol) and 3-dimethylamino-propyl)-ethyl-carbodiimide hydrochloride (1.33 g, 6.95 mmol) in THF (20 mL) is added 2-(3,4-dimethoxy-phenyl)-ethylamine (1.20 g, 6.62 mmol). The mixture is stirred at rt for 14 h. The mixture is poured onto H2O (100 mL) and EtOAc (100 mL). The organic layer is washed successively with saturated sodium hydrogen carbonate solution, 10% citric acid and saturated sodium chloride solution. The resulting organic layer is concentrated under reduced pressure to give the title compound.

Workup

  1. washThe organic layer is washed successively with saturated sodium hydrogen carbonate solution, 10% citric acid and saturated sodium chloride solution
  2. concentrationThe resulting organic layer is concentrated under reduced pressure

Sources & evidence

ORD record
ord-51fef4e47757433e99055c3ecf39763c
Source dataset
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06815451B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes