Reaktion #54057

Reaktionsgleichung

EDC

HOBT

benzoic acid

4-aminomethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline

Diisopropyl ethyl amine

→

title compound

Ausbeute 22.1%

N-[6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethyl]benzamide

Ausbeute 22.1%

Lösungsmittel

methylene chloride

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA round bottom flask equipped with a stir bar
2. 2
   SonstigeThe crude reaction mixture
3. 3
   Sonstigewas transferred to a separatory funnel
4. 4
   Waschenwashed with 1 N HCl, aqueous saturated sodium bicarbonate (NaHCO3) solution, and brine
5. 5
   EinengenThe organics were concentrated in vacuo
6. 6
   Sonstigeto afford a brown oil
7. 7
   SonstigeThe product was purified by column chromatography
8. 8
   Einengenconcentrated in vacuo

Vorschrift

A round bottom flask equipped with a stir bar was charged with EDC (0.224 mmol, 1.1 equiv), HOBT (0.224 mmol, 1.1 equiv), benzoic acid (0.224 mmol, 1.1 equiv), 4-aminomethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline (0.204 mmol, 1 equiv) and 3.3 mL of methylene chloride. Diisopropyl ethyl amine (0.224 mmol, 1.1 equiv) was added last, the reaction was placed under argon, and stirred at room temperature overnight. The crude reaction mixture was transferred to a separatory funnel, diluted with EtOAc, and washed with 1 N HCl, aqueous saturated sodium bicarbonate (NaHCO3) solution, and brine. The organics were concentrated in vacuo to afford a brown oil. The product was purified by column chromatography using silica gel eluting with a gradient of 10-50% EtOAc/hexanes. The product fractions were pooled and concentrated in vacuo to afford 18 mg of the title compound as a yellow oil.

Quelle