Ethyl Acetate → 2-Benzyloxy-1-[4-(2,4-dichloro-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-ethanone

HRID 544958Notes

Reaction equation

HRID 544958 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([N:12]1[CH2:17][CH2:16][C:15]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[Cl:26])(O)[CH2:14][CH2:13]1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O>[CH2:1]([O:8][CH2:9][C:10]([N:12]1[CH2:13][CH:14]=[C:15]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[Cl:26])[CH2:16][CH2:17]1)=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 575503582-Benzyloxy-1-[4-(2,4-dichloro-phenyl)-4-hydroxy-piperidin-1-yl]-ethanone

Product 1

HCID 575503572-Benzyloxy-1-[4-(2,4-dichloro-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-ethanoneYield 28%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2-benzyloxy-1-[4-(2,4-dichloro-phenyl)-4-hydroxy-piperidin-1-yl]-ethanone (0.035 g, 0.09 mmol) in trifluoroacetic acid (1 mL) was stirred at RT for 48 h. Ethyl acetate (2 mL) and saturated aqueous sodium bicarbonate (2 mL) were added and the layers were separated. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The isolated residue was chromatographed on silica gel using dichloromethane/ethyl acetate to 100% to 90% dichloromethane in a gradient fashion, to give the title compound as a gum (0.0094 g, 28%).

Workup

  1. customthe layers were separated
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe isolated residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-853663d46c154a1c992d6e4bb7681503
Source dataset
uspto-grants-2011_05
Patent number
US07935703B2

Reaction notes

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