Ethanol → HCID 178472385, compound

HRID 969550Notes

Reaction equation

HRID 969550 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH:12]2[CH2:17][CH2:16][CH:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]2)[CH2:8][CH2:7]1.[O-]CC.[Na+].[Na].C(O)C>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[O:5][CH:6]1[CH2:7][CH2:8][N:9]([C@H:12]2[CH2:13][CH2:14][C@H:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:16][CH2:17]2)[CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 17963321HCID 17963321, compound

Product 1

HCID 178472385HCID 178472385, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 4-[4-(3,4-dichlorophenoxy)-1-piperidinyl]-cyclohexanecarboxylate (method F, step a, 0.97 g) was added to a solution of sodium ethoxide prepared from sodium (1.28 g) and ethanol (100 ml). The resultant solution was heated under reflux for 18 h. Acetic acid (0.1 ml) was added and the solvent was evaporated. Ethyl acetate, water and sodium hydroxide were added to the residue and separated. The aqueous phase was extracted twice with ethyl acetate-methanol mixtures and the combined organic phases were washed with brine, dried (MgSO4), filtered and evaporated to give the subtitle compound as an oil.

Workup

  1. temperatureunder reflux for 18 h
  2. customthe solvent was evaporated
  3. additionEthyl acetate, water and sodium hydroxide were added to the residue
  4. customseparated
  5. extractionThe aqueous phase was extracted twice with ethyl acetate-methanol mixtures
  6. washthe combined organic phases were washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-39345354f4a34b29ba087d8529347aa5
Source dataset
uspto-grants-2007_12
Patent number
US07307090B2

Reaction notes

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