Reaktion #67959

Reaktionsgleichung

N,N-dimethylformamide

(3-bromopropyl)benzene

potassium carbonate

1-(trifluoroacetyl)piperidine-4-amine hydrochloride

→

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

Lösungsmittel

water

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   SonstigeThe organic layer was separated
3. 3
   Waschenwashed sequentially with water
4. 4
   Trocknenan aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
5. 5
   Sonstigethe 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
   SonstigeThe organic layer was separated
9. 9
   Waschenwashed sequentially with water
10. 10
    Trocknenan aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate
11. 11
    Sonstigethe solvent was removed under reduced pressure

Vorschrift

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.

Quelle