Reaktion #2341485

Reaktionsgleichung

2,3-Dihydro-6,7-methylenedioxy-1,4-benzodioxin-2-methanamine

5-(3-bromopropoxy)quinoline

diisopropylethylamine

→

title compound

Ausbeute 38.6%

N-[3-(Quinolin-5-yloxy)propyl]-2,3-dihydro-6,7-methylenedioxy-1,4-benzodioxin-2-methanamine

Ausbeute 38.6%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was then removed in vacuum
2. 2
   WaschenThe mixture was washed with 250 ml each of saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
3. 3
   Trocknendried over sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacuum
6. 6
   Sonstigechromatographed on 250 g of silica gel using 2% methanol/dichloromethane as eluant
7. 7
   Einengenconcentrated in vacuum
8. 8
   Sonstigethe residue (2.0 g) recrystallized from 50 ml of ethanol with the addition of 6 ml of 4N isopropanolic HCl

Vorschrift

2,3-Dihydro-6,7-methylenedioxy-1,4-benzodioxin-2-methanamine (2.3 g, 11 mmole), 5-(3-bromopropoxy)quinoline (2.54 g, 9.2 mmole), and diisopropylethylamine (2.6 g, 20 mmole) were combined in 100 ml of DMF and heated at 80° C. for 24 hours under a nitrogen atmosphere. The solvent was then removed in vacuum and replaced with 500 ml of dichloromethane. The mixture was washed with 250 ml each of saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over sodium sulfate, filtered, and concentrated in vacuum. The residue was column chromatographed on 250 g of silica gel using 2% methanol/dichloromethane as eluant. The product-containing fractions were combined and concentrated in vacuum and the residue (2.0 g) recrystallized from 50 ml of ethanol with the addition of 6 ml of 4N isopropanolic HCl to give 1.4 g of the title compound as an orange solid dihydrochloride, one-quarter hydrate, m.p. 140°-145° C.

Quelle