Réaction #992749

Équation de réaction

bicarbonate

2-Bromo-6-trifluoromethyl-benzene-1,4-diamine

bis-(2-bromoethyl)ether

N,N-diisopropyl-ethylamine

→

title compound

Rendement 63.0%

2-Bromo-4-morpholin-4-yl-6-trifluoromethyl-phenylamine

Rendement 63.0%

Solvants

N,N-dimethylformamide

Conditions de réaction

Traitement

1. 1
   Extractionthe crude mixture was extracted with ethyl acetate (100 mL)
2. 2
   LavageThe organic phase was washed with water (100 mL) and brine (100 mL)
3. 3
   Séchagedried over sodium sulfate
4. 4
   Concentrationconcentrated in vacuo
5. 5
   AutreThe crude product was purified by flash chromatography

Mode opératoire

2-Bromo-6-trifluoromethyl-benzene-1,4-diamine (2.21 g), bis-(2-bromoethyl)ether (1.30 mL) and N,N-diisopropyl-ethylamine (4.64 mL) were mixed in N,N-dimethylformamide (19 mL) and heated to 180° C. for 30 minutes in a sealed microwave process vial. Saturated aqueous bicarbonate (100 mL) was added and the crude mixture was extracted with ethyl acetate (100 mL). The organic phase was washed with water (100 mL) and brine (100 mL), dried over sodium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography to furnish 1.78 g (63%) of the title compound as a yellow solid. LC-MS (m/z) 326 (MH+); tR=2.54, (UV, ELSD) 83%, 75%. 1H NMR (500 MHz, DMSO-d6): 2.99 (m, 4H), 3.70 (m, 4H), 5.00 (s, 2H), 7.00 (d, 1H), 7.38 (d, 1H).

Source