Benzeneacetic acid, 3,4-dimethoxy-, methyl ester → N-(3,4-dimethoxybenzyl)-2-(3-methylphenyl) ethylamine

HRID 1108907

Reaction equation

HRID 1108907 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11]C(OC)=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:16][C:17]1[CH:18]=[C:19]([CH2:23][CH2:24][NH2:25])[CH:20]=[CH:21][CH:22]=1>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])[CH2:11][NH:25][CH2:24][CH2:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([CH3:16])[CH:18]=1

Participants

4

Reactant 2

HCID 85213Benzeneacetic acid, 3,4-dimethoxy-, methyl esterHCID 4100852-(3-Methylphenyl)ethan-1-amine

Product 1

HCID 54124366N-(3,4-dimethoxybenzyl)-2-(3-methylphenyl) ethylamineYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 3,4-dimethoxyphenylacetate (18.5 g, 0.088 mole) and 2-(3-methylphenyl) ethylamine was heated at 180° for 1 h. The crude amide was dissolved in 50 ml of methanol and precipitated as fine needles with 150 ml of hexane to give the title compound (20.4 g, 74%). The mother liquor deposited more material which was recrystallized from toluene (charcoal) to give an additional 4.7 g (17%) of amide. The total yield of N-(3,4-dimethoxyphenylacetyl)-2-(3-methylphenyl) ethylamine, mp 101°-102°, was 91%.

Workup

  1. customprecipitated as fine needles with 150 ml of hexane

Sources & evidence

ORD record
ord-8c084d7069a5400e87a758a8756a8830
Source dataset
uspto-grants-1994_06
Patent number
USRE034630

Linked notes

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