Chloroacetyl chloride → 1,1-Dimethylethyl 4-(3-oxo-4-morpholinyl)-1-piperidinecarboxylate

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 4-(2-hydroxyethyl)amino-1-piperidinecarboxylate (2.4 g) obtained in Example 91a) and triethylamine (1.0 g) were dissolved in THF (70 ml). While the mixture was cooled to 0° C., chloroacetyl chloride (0.72 ml) was added dropwise thereto, and mixed at 0° C. for 2 hours. Sodium hydride (60%; 1.0 g) and DMF (30 ml) were added to the reaction mixture, and mixed at 80° C. for 15 hours. The reaction mixture was concentrated under reduced pressure, water was added thereto, and then extracted with ethyl acetate. The extract was washed with water, a 5% aqueous citric acid solution and saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified with silica gel column (ethyl acetate/hexane=1/1 to ethyl acetate) to obtain the title compound as a colorless oil (0.51 g, 18%).

Provenance & Evidence