Methanol → Tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamate

HRID 2193045Notes

Reaction equation

HRID 2193045 reaction equation
CO.[C:3]([O:7][C:8](=[O:33])[N:9]([CH2:22][C:23]1[CH:32]=[CH:31][C:26]2[O:27][CH2:28][CH2:29][O:30][C:25]=2[CH:24]=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:3]([O:7][C:8](=[O:33])[N:9]([CH2:22][C:23]1[CH:32]=[CH:31][C:26]2[O:27][CH2:28][CH2:29][O:30][C:25]=2[CH:24]=1)[CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 57815287HCID 57815287, compound

Product 1

HCID 57815320Tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 20 mL of a methanol solution containing 1.4 g of tert-butyl(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(trifluoroacetyl)piperidin-4-yl)carbamate, 5 mL of water and 0.53 g of potassium carbonate were added, and the mixture was stirred at room temperature for 1 hour and 15 minutes. The solvent was removed under reduced pressure, and ethyl acetate and water were added thereto. 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 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 1.0 g of a pale yellow oily substance, tert-butyl(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamate.

Workup

  1. additionwere added
  2. customThe solvent was removed under reduced pressure, and ethyl acetate and water
  3. additionwere added
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washthe resultant solution was washed sequentially with water
  7. dry with materialan aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-13aba8dbfe0846d28bfc993cfc22080e
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

Loading…