Methanol → Tert-butyl(3-phenylpropyl)(piperidin-4-yl)carbamate

HRID 2193054Notes

Reaction equation

HRID 2193054 reaction equation
CO.[C:3]([O:7][C:8](=[O:31])[N:9]([CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:10]1[CH2:15][CH2:14][N:13](C(=O)C(F)(F)F)[CH2:12][CH2:11]1)([CH3:6])([CH3:5])[CH3:4].C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C>[C:3]([O:7][C:8](=[O:31])[N:9]([CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:10]1[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]1)([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 3

HCID 887Methanol2×HCID 11430Potassium CarbonateHCID 59397931Tert-butyl(3-phenylpropyl)(1-(trifluoroacetyl)piperidin-4-yl)carbamate

Product 1

HCID 59398435Tert-butyl(3-phenylpropyl)(piperidin-4-yl)carbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To 2 mL of a methanol solution containing 0.60 g of tert-butyl(3-phenylpropyl)(1-(trifluoroacetyl)piperidin-4-yl)carbamate, 0.4 mL of water was added, and 0.28 g of potassium carbonate was added under cooling with ice, and the mixture was stirred at the same temperature for 2 hours and 10 minutes and at room temperature for 2 hours and 15 minutes. Thereto was added 2 mL of methanol and 0.5 mL of water, and the mixture was left to stand at room temperature overnight. The solvent was removed under reduced pressure, and the residue thus obtained was added with ethyl acetate and water. 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 to obtain 0.45 g of a colorless oily substance, tert-butyl(3-phenylpropyl)(piperidin-4-yl)carbamate.

Workup

  1. additionwas added
  2. temperatureunder cooling with ice
  3. waitthe mixture was left
  4. waitto stand at room temperature overnight
  5. customThe solvent was removed under reduced pressure
  6. customthe residue thus obtained
  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

Sources & evidence

ORD record
ord-e01bcad14e7545dca06dca1c4d12037a
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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