Water → HCID 57888694, compound

HRID 1820237Notes

Reaction equation

HRID 1820237 reaction equation
C([NH:4][C:5]1([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH2:10][CH2:9][N:8](C(OCC)=O)[CH2:7][C:6]1([CH3:17])[CH3:16])(=O)C.[OH-].[Na+].O>C(O)C>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:5]2([NH2:4])[CH2:10][CH2:9][NH:8][CH2:7][C:6]2([CH3:16])[CH3:17])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 57889422HCID 57889422, compound

Product 1

HCID 57888694HCID 57888694, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 4-acetamido-4-(4-chlorophenyl)-3,3-dimethylpiperidine-1-carboxylate (2.04 g, 5.78 mmol) in ethanol (25 mL) was treated with 5 N NaOH (aq) (23.13 mL, 116 mmol), and the mixture was heated at reflux for two days. During the reflux, a colorless, soapy solid predipitated. Water was added until a clear solution was observed. The ethanol was removed under reduced pressure, and the aqueous mixture was extracted 4× with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated in-vacuo to yield the title compound (1.28 g, 5.36 mmol, 93% yield) as a colorless powder. MS (ESI+)=239, (M+H)+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for two days
  3. customThe ethanol was removed under reduced pressure
  4. extractionthe aqueous mixture was extracted 4× with ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-f84848c287504b34969fb20687f0f2b7
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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