Reaction #67958

Reaction equation

N,N-dimethylformamide

2-(2-bromoethylthio)thiophene

potassium carbonate

1-(trifluoroacetyl)piperidine-4-amine hydrochloride

potassium carbonate

→

N-(2-(2-thienylthio)ethyl)-1-(trifluoroacetyl)piperidine-4-amine

Solvents

water

ethyl acetate

Conditions

Workup

1. 1
   workup.ADDITIONwere added
2. 2
   Temperatureunder cooling with ice
3. 3
   Temperatureunder cooling with ice
4. 4
   workup.STIRRINGthe mixture was stirred for 45 minutes
5. 5
   workup.STIRRINGstirred at 70° C. for 3 hours
6. 6
   TemperatureThe reaction mixture was cooled to room temperature
7. 7
   OtherThe organic layer was separated
8. 8
   Washwashed with an aqueous saturated sodium chloride solution
9. 9
   Dryingdried over anhydrous magnesium sulfate
10. 10
    Otherthe solvent was removed under reduced pressure
11. 11
    OtherThe residue thus obtained
12. 12
    Otherwas purified by silica gel column chromatography [eluent; chloroform:methanol=50:1]

Procedure

To 2 mL of an N,N-dimethylformamide solution containing 0.14 g of 2-(2-bromoethylthio)thiophene, 95 mg of potassium carbonate and 0.16 g of 1-(trifluoroacetyl)piperidine-4-amine hydrochloride were added under cooling with ice, and the mixture was stirred at room temperature for 40 minutes. Thereto was added 95 mg of potassium carbonate under cooling with ice, and the mixture was stirred for 45 minutes, and stirred at 70° C. for 3 hours. The reaction mixture was cooled to room temperature, and then ethyl acetate and water were added thereto. The organic layer was separated, washed with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:methanol=50:1] to obtain 62 mg of a yellow oily substance, N-(2-(2-thienylthio)ethyl)-1-(trifluoroacetyl)piperidine-4-amine.

Source