1,1'-Carbonyldiimidazole → N-[3-(3,4-Dimethoxyphenyl) propionyl]-2-(3-methylphenyl) ethylamine

HRID 1108908

Reaction equation

HRID 1108908 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]([OH:15])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:28][C:29]1[CH:30]=[C:31]([CH2:35][CH2:36][NH2:37])[CH:32]=[CH:33][CH:34]=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]([NH:37][CH2:36][CH2:35][C:31]2[CH:32]=[CH:33][CH:34]=[C:29]([CH3:28])[CH:30]=2)=[O:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 750193-(3,4-Dimethoxyphenyl)propionic acidHCID 4100852-(3-Methylphenyl)ethan-1-amine

Product 1

HCID 15068909N-[3-(3,4-Dimethoxyphenyl) propionyl]-2-(3-methylphenyl) ethylamineYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(3,4-dimethoxyphenyl) propionic acid (21 g, 0.10 mol) and 16.4 g (0.101 mol) of carbonyldimidazole in dry THF was stirred for 1 h in a flask protected from moisture. To this solution was added 2-(3-methylphenyl)ethylamine (14.2 g, 0.105 mol) and stirring was continued for 50 min. The solvent was evaporated and the residue was triturated with water and collected by filtration. The crude amide was recrystallized from methanol-water to give 28.6 g (88%) of the title compound mp 100°-103°.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was triturated with water
  3. filtrationcollected by filtration
  4. customThe crude amide was recrystallized from methanol-water

Sources & evidence

ORD record
ord-5748fe82dd72422e8a7aabdd2292735b
Source dataset
uspto-grants-1994_06
Patent number
USRE034630

Linked notes

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