Reaktion #350564

Reaktionsgleichung

HCl

3-Morpholinecarboxylic acid

4-chloro-2-fluoro-5-(1-methylethoxy)aniline

trimethylaluminum

→

title compound

Ausbeute 43.5%

N-[4-Chloro-2-fluoro-5-(1-methylethoxy)phenyl]morpholine-3-carboxamide

Ausbeute 43.5%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resultant reaction mixture
2. 2
   workup.STIRRINGwas stirred at room temperature for 2 days
3. 3
   SonstigeThe solid formed
4. 4
   Filtrationwas filtered off
5. 5
   workup.ADDITION400 mL of CH2Cl2 was added
6. 6
   SonstigeThe organic layer was separated
7. 7
   Trocknendried over MgSO4
8. 8
   Sonstigethe solvent was removed under vacuum

Vorschrift

To a stirring solution of 4-chloro-2-fluoro-5-(1-methylethoxy)aniline (15.52 g, 76.26 mmol) in CH2Cl2 (100 mL), under nitrogen at 0° C. (ice-bath) was added dropwise trimethylaluminum (114.4 mL, 228.78 mmol). The mixture was then stirred overnight at room temperature. 3-Morpholinecarboxylic acid (10.0 g, 76.20 mmol) was added portionwise at room temperature. The resultant reaction mixture was stirred at room temperature for 2 days. 6N HCl was added dropwise to the reaction mixture at 0° C. (ice-bath). The solid formed was filtered off and suspended in water (100 mL). The suspension was basicified with 50% aqueous NaOH to pH 13. 400 mL of CH2Cl2 was added. The organic layer was separated, dried over MgSO4 and the solvent was removed under vacuum to give the title compound of Step B as a white solid (10.5 g), m.p. 99°-101° C. 1H NMR: δ9.30 (br s,1H), 8.17 (d,1H), 7.14 (d,1H), 4.53 (q,1H), 3.96-3.61 (m,5H), 3.00-3.01 (m,2H), 1.37 (d,6H).

Quelle