Dimethylformamide → n-(2-(2-Thienylthio)ethyl)-1-(trifluoroacetyl)piperidine-4-amine

HRID 2193052Notes

Reaction equation

HRID 2193052 reaction equation
CN(C)C=O.Br[CH2:7][CH2:8][S:9][C:10]1[S:11][CH:12]=[CH:13][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[F:22][C:23]([F:34])([F:33])[C:24]([N:26]1[CH2:31][CH2:30][CH:29]([NH2:32])[CH2:28][CH2:27]1)=[O:25]>O.C(OCC)(=O)C>[S:11]1[CH:12]=[CH:13][CH:14]=[C:10]1[S:9][CH2:8][CH2:7][NH:32][CH:29]1[CH2:28][CH2:27][N:26]([C:24](=[O:25])[C:23]([F:22])([F:33])[F:34])[CH2:31][CH2:30]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium Carbonate2×HCID 122011192-(2-Bromoethylthio)-thiopheneHCID 866331901-(4-Aminopiperidin-1-YL)-2,2,2-trifluoroethan-1-one hydrochloride

Product 1

HCID 59398283n-(2-(2-Thienylthio)ethyl)-1-(trifluoroacetyl)piperidine-4-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

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.

Workup

  1. additionwere added
  2. temperatureunder cooling with ice
  3. temperatureunder cooling with ice
  4. stirringthe mixture was stirred for 45 minutes
  5. stirringstirred at 70° C. for 3 hours
  6. temperatureThe reaction mixture was cooled to room temperature
  7. customThe organic layer was separated
  8. washwashed with an aqueous saturated sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was removed under reduced pressure
  11. customThe residue thus obtained
  12. customwas purified by silica gel column chromatography [eluent; chloroform:methanol=50:1]

Sources & evidence

ORD record
ord-5dababb8fde24237858d0428a6b5cc0e
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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