Reaktion #360999

Reaktionsgleichung

HCl

2,3-Dihydro-1,4-benzodioxin-2-methanamine

5-chloro-N-[4-(trifluoromethyl)phenyl]-pentanamide

Sodium bicarbonate

potassium iodide

sodium bicarbonate

→

title compound

Ausbeute 12.4%

5-[(2,3-Dihydro-1,4-benzodioxin-2-yl)methylamino]-N-[4-(trifluoromethyl)phenyl]-pentanamide, monohydrochloride

Ausbeute 12.4%

Lösungsmittel

ethanol

dimethylformamide

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture extracted with diethyl ether (3×30 mL)
2. 2
   TrocknenThe combined extracts were dried (MgSO4)
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigeThe resulting oil was chromatographed
6. 6
   Wascheneluting with 40:60 ethyl acetate
7. 7
   Sonstigehexane, then 10:90 ethanol:ethyl acetate to give a yellow-white solid with an Rf of 0.15 in 50:50 ethyl acetate
8. 8
   EinengenThe solution was concentrated in vacuo to a white solid which
9. 9
   Sonstigeafter recrystallization from ethanol

Vorschrift

2,3-Dihydro-1,4-benzodioxin-2-methanamine (350 mg) and 5-chloro-N-[4-(trifluoromethyl)phenyl]-pentanamide (593 mg) were stirred in dimethylformamide (7.0 mL) under a nitrogen atmosphere. Sodium bicarbonate (395 mg) and potassium iodide (40 mg) were added and mixture was stirred for 60 hours at 70°-75° C. Saturated sodium bicarbonate solution (50 mL) was added to the cooled reaction and the mixture extracted with diethyl ether (3×30 mL). The combined extracts were dried (MgSO4), filtered, and concentrated in vacuo. The resulting oil was chromatographed eluting with 40:60 ethyl acetate:hexane, then 10:90 ethanol:ethyl acetate to give a yellow-white solid with an Rf of 0.15 in 50:50 ethyl acetate:ethanol. This solid was dissolved in ethanol (20 mL) and treated with 1.0M aqueous HCl (1.0 mL). The solution was concentrated in vacuo to a white solid which after recrystallization from ethanol:ethyl acetate afforded the title compound as a white powder (117 mg).

Quelle