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

HRID 1031906

Reaktionsgleichung

Reaktionsgleichung von HRID 1031906
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 3-(3,4-dimethoxyphenyl) propionic acid (21 g, 0.10 mol) and 16.4 g (0.101 mol) of carbonyldiimidazole 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°.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2f8051cae4bd41a28eeb9872f21c31fe
Quelldatensatz
uspto-grants-1990_09
Patentnummer
US04956371

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