Dimethylformamide → HCID 57815210, compound

Participants

Reaction Steps

To a solution of 0.50 g of 1-(trifluoroacetyl)piperidin-4-amine in 10 mL of a mixed solvent of N,N-dimethylformamide and tetrahydrofuran (1:1), 0.41 g of potassium carbonate, 0.42 mL of propargyl bromide were added, and the mixture was heated under reflux while stirring for 2 hours. Thereto were added water and ethyl acetate, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with water and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 0.60 g of N-(2-propyn-1-yl)-1-(trifluoroacetyl)piperidin-4-amine as a crude product (crude product A). On the other hand, to a solution of 0.70 g of 1-(trifluoroacetyl)piperidin-4-amine in 7.2 mL of a mixed solvent of N,N-dimethylformamide and tetrahydrofuran (1:1), 0.59 g of potassium carbonate, and 0.30 mL of propargyl bromide were added, and the mixture was heated under reflux while stirring for 1 hour 50 minutes. Thereto were added water and ethyl acetate, and mixed with 0.60 g of the crude product A obtained above, and the mixture was adjusted to pH 1 with 6 mol/L hydrochloric acid. The aqueous layer was separated, and washed with ethyl acetate, ethyl acetate was added thereto, and the aqueous layer was saturated with potassium carbonate. The organic layer was separated, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.0 g of N-(2-propyn-1-yl)-1-(trifluoroacetyl)piperidin-4-amine as a brown oily substance.

Provenance & Evidence