Ethanol → 4-(4-Ethoxymethyl-5-phenyl-oxazol-2-yl)-piperidine

HRID 2288958Notes

Reaction equation

HRID 2288958 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([CH:14]2[CH2:19][CH2:18][N:17](C(=O)C)[CH2:16][CH2:15]2)[O:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+].[CH2:25]([OH:27])[CH3:26]>O>[CH2:25]([O:27][CH2:2][C:3]1[N:4]=[C:5]([CH:14]2[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]2)[O:6][C:7]=1[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH3:26]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 187004361-[4-(4-Chloromethyl-5-phenyl-oxazol-2-yl)-piperidin-1-yl]ethanone

Product 1

HCID 187004234-(4-Ethoxymethyl-5-phenyl-oxazol-2-yl)-piperidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1-[4-(4 -chloromethyl-5-phenyl-oxazol-2-yl)-piperidin-1-yl]-ethanone (0.200 g, 0.627 mmol), prepared as in intermediate 3B, in ethanol (4.5 ml) is treated with a solution of NaOH (0.501 g, 12.55 mmol) in water (1/.5 ml). The reaction mixture is heated to 75 C for 48 hours, concentrated, and the residue partitioned between EtOAc and water. The aqueous phase is washed with EtOAc (twice). The organic phases are combined and washed with saturated brine, dried (Na2SO4) and concentrated to afford the title compound as a light orange oil.

Workup

  1. temperatureThe reaction mixture is heated to 75 C for 48 hours
  2. concentrationconcentrated
  3. customthe residue partitioned between EtOAc and water
  4. washThe aqueous phase is washed with EtOAc (twice)
  5. washwashed with saturated brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4ad37e2424214caf818e7dc38e70c827
Source dataset
uspto-grants-2000_07
Patent number
US06090825

Reaction notes

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