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

HRID 1031905

Reaktionsgleichung

Reaktionsgleichung von HRID 1031905
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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%.

Aufarbeitung

  1. customprecipitated as fine needles with 150 ml of hexane

Quellen und Nachweise

ORD-Eintrag
ord-cb6c4b9983344d488cecaf73117b8042
Quelldatensatz
uspto-grants-1990_09
Patentnummer
US04956371

Verknüpfte Notizen

Wird geladen…