Methyl 3,4-Dimethoxybenzoate → N-(3,4-Dimethoxybenzoyl)-2-(3-methylphenyl) ethylamine

HRID 1031903

Reaction equation

HRID 1031903 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH2:10])[CH:5]=[CH:6][CH:7]=1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:16](OC)=[O:17]>C(Cl)Cl>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:16]([NH:10][CH2:9][CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=1)=[O:17]

Participants

4

Reactant 2

HCID 16522Methyl 3,4-DimethoxybenzoateHCID 4100852-(3-Methylphenyl)ethan-1-amine

Product 1

HCID 15068903N-(3,4-Dimethoxybenzoyl)-2-(3-methylphenyl) ethylamineYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 2-(3-methylphenyl) ethylamine (28.3 g, 0.21 mol) and 36.9 g of methyl 3,4-dimethoxybenzoate (36.9 g, 0.19 mol) was heated at 180° for 4 h. The crude amide was taken up in CH2Cl2 and washed with dilute HCl, dilute Na2CO3 and water. Chromatography over neutral alumina afforded 29 g (51%) of the title compound (one spot by tlc) eluted with CH2Cl2. The analytical sample showed mp 108-109° after crystallization from i-PrOH.

Workup

  1. washwashed with dilute HCl, dilute Na2CO3 and water

Sources & evidence

ORD record
ord-307152a5bf0646629545ac2167f2346f
Source dataset
uspto-grants-1990_09
Patent number
US04956371

Linked notes

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