Dimethylformamide → HCID 59398055, compound

HRID 39681Notes

Reaction equation

HRID 39681 reaction equation
CN(C)C=O.Br[CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[F:23][C:24]([F:35])([F:34])[C:25]([N:27]1[CH2:32][CH2:31][CH:30]([NH2:33])[CH2:29][CH2:28]1)=[O:26]>O.C(OCC)(=O)C>[C:10]1([CH2:9][CH2:8][CH2:7][NH:33][CH:30]2[CH2:29][CH2:28][N:27]([C:25](=[O:26])[C:24]([F:23])([F:34])[F:35])[CH2:32][CH2:31]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 12503(3-Bromopropyl)benzeneHCID 866331901-(4-Aminopiperidin-1-YL)-2,2,2-trifluoroethan-1-one hydrochloride

Product 1

HCID 59398055HCID 59398055, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  1. additionwere added
  2. customThe organic layer was separated
  3. washwashed sequentially with water
  4. dry with materialan aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. stirringthe mixture was stirred at room temperature for 15 minutes
  7. additionThe reaction mixture was added with ethyl acetate and water
  8. customThe organic layer was separated
  9. washwashed sequentially with water
  10. dry with materialan aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate
  11. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-57d79dbed41d4a9883350f76014bf2ec
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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