Reacción #67959

Ecuación de reacción

N,N-dimethylformamide

(3-bromopropyl)benzene

potassium carbonate

1-(trifluoroacetyl)piperidine-4-amine hydrochloride

→

N-(3-phenylpropyl)-1-(trifluoroacetyl)piperidine-4-amine

Disolventes

water

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwere added
2. 2
   OtroThe organic layer was separated
3. 3
   Lavadowashed sequentially with water
4. 4
   Secadoan aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
5. 5
   Otrothe solvent was removed under reduced pressure
6. 6
   workup.STIRRINGthe mixture was stirred at room temperature for 15 minutes
7. 7
   workup.ADDITIONThe reaction mixture was added with ethyl acetate and water
8. 8
   OtroThe organic layer was separated
9. 9
   Lavadowashed sequentially with water
10. 10
    Secadoan aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate
11. 11
    Otrothe solvent was removed under reduced pressure

Procedimiento

To 2 mL of an N,N-dimethylformamide solution containing 0.38 mL of (3-bromopropyl)benzene, 0.76 g of potassium carbonate and 0.64 g of 1-(trifluoroacetyl)piperidine-4-amine hydrochloride were added, and the mixture was stirred at room temperature for 2 hours and 30 minutes. The reaction mixture was added with ethyl acetate and water. The organic layer was separated, washed sequentially with water and an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. Thereto were further added 2 mL of N,N-dimethylformamide, 0.40 g of 1-(trifluoroacetyl)piperidine-4-amine dihydrochloride and 0.60 g of potassium carbonate, and the mixture was stirred at room temperature for 15 minutes. The reaction mixture was added with ethyl acetate and water. The organic layer was separated, washed sequentially with water and an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 0.99 g of a yellow oily substance, N-(3-phenylpropyl)-1-(trifluoroacetyl)piperidine-4-amine. (2) To 3 mL of a dichloromethane solution containing 0.99 g of N-(3-phenylpropyl)-1-(trifluoroacetyl)piperidine-4-amine, 0.82 g of di-tert-butyl dicarbonate was added under cooling with ice, and the mixture was stirred at the same temperature for 30 minutes and at room temperature for 1 hour. Thereto was further added 0.20 g of di-tert-butyl dicarbonate, and the mixture was left to stand at room temperature overnight. The solvent was removed under reduced pressure, and the residue thus obtained was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1] to obtain 0.63 g of a colorless oily substance, tert-butyl (3-phenylpropyl) (1-(trifluoroacetyl)piperidin-4-yl)carbamate.

Fuente