Methyl 3,4,5-trimethoxybenzoate → N-(3,4,5-Trimethoxybenzoyl)-2-(3-methylphenyl) ethylamine

HRID 1031907Notes

Reaction equation

HRID 1031907 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([O:15][CH3:16])[C:12]=1[O:13][CH3:14])[C:6]([O:8]C)=O.[CH3:17][C:18]1[CH:19]=[C:20]([CH2:24][CH2:25][NH2:26])[CH:21]=[CH:22][CH:23]=1>C(Cl)Cl>[CH3:16][O:15][C:11]1[CH:10]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:12]=1[O:13][CH3:14])[C:6]([NH:26][CH2:25][CH2:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([CH3:17])[CH:19]=1)=[O:8]

Participants

4

Reactant 2

HCID 15956Methyl 3,4,5-trimethoxybenzoateHCID 4100852-(3-Methylphenyl)ethan-1-amine

Product 1

HCID 15068911N-(3,4,5-Trimethoxybenzoyl)-2-(3-methylphenyl) ethylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 3,4,5-trimethoxybenzoate (31.1 g, 0.138 mol) and 2-(3-methylphenyl)ethylamine (18.6 g, 0.138 mol) was heated at 180° for 6 h. The dark reaction mixture was taken up in methylene chloride and washed with dilute HCl. The solvent was evaporated and the residue was chromatographed on 150 g of neutral alumina. Elution with methyl chloride/hexane (3:1) removed some by-products and elution with methylene chloride gave nearly pure amide F1 which was recrystallized from i-PrOH to give pure F1 (5.2 g, 11%), mp 105-108°.

Workup

  1. customThe dark reaction mixture
  2. washwashed with dilute HCl
  3. customThe solvent was evaporated
  4. customthe residue was chromatographed on 150 g of neutral alumina
  5. washElution with methyl chloride/hexane (3:1)
  6. customremoved
  7. washsome by-products and elution with methylene chloride

Sources & evidence

ORD record
ord-de69687b44524a318464f031631098d0
Source dataset
uspto-grants-1990_09
Patent number
US04956371

Reaction notes

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