Réaction #992751

Équation de réaction

bicarbonate

2,5-Diamino-3-chloro-benzonitrile

bis-(2-bromoethyl)ether

N,N-diisopropyl-ethylamine

→

title compound

Rendement 91.0%

2-Amino-3-chloro-5-morpholin-4-yl-benzonitrile

Rendement 91.0%

Solvants

N,N-dimethylformamide

Conditions de réaction

Traitement

1. 1
   Extractionthe crude mixture was extracted with ethyl acetate (20 mL)
2. 2
   LavageThe organic phase was washed with water (20 mL) and brine (20 mL)
3. 3
   Séchagedried over sodium sulfate
4. 4
   Concentrationconcentrated in vacuo

Mode opératoire

2,5-Diamino-3-chloro-benzonitrile (387 mg), bis-(2-bromoethyl)ether (0.35 mL) and N,N-diisopropyl-ethylamine (1.25 mL) were mixed in N,N-dimethylformamide (4 mL) and heated to 180° C. for 30 minutes in a sealed microwave process vial. Saturated aqueous bicarbonate (20 mL) was added and the crude mixture was extracted with ethyl acetate (20 mL). The organic phase was washed with water (20 mL) and brine (20 mL), dried over sodium sulfate and concentrated in vacuo to furnish 0.50 g (91%) of the title compound as a brown solid. LC-MS (m/z) 238 (MH+); tR=2.31, (UV, ELSD) 85%, 95%. 1H NMR (500 MHz, DMSO-d6): 2.97 (m, 4H), 3.69 (m, 4H), 5.59 (s, 2H), 7.04 (d, 1H), 7.29 (d, 1H).

Source