Dimethylformamide → HCID 57815210, compound

HRID 385573Notes

Reaction equation

HRID 385573 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([NH2:11])[CH2:7][CH2:6]1)=[O:4].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[CH2:25](Br)[C:26]#[CH:27]>C(OCC)(=O)C.O.O1CCCC1>[CH2:27]([NH:11][CH:8]1[CH2:9][CH2:10][N:5]([C:3](=[O:4])[C:2]([F:1])([F:12])[F:13])[CH2:6][CH2:7]1)[C:26]#[CH:25]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 450809161-(4-Aminopiperidin-1-yl)-2,2,2-trifluoroethan-1-one

Product 1

HCID 57815210HCID 57815210, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washthe resultant solution was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e37987ab52c14302927edb00bfb71ebb
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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