1-Benzyl-4-piperidone → HCID 131722813, compound

HRID 1386779Notes

Reaction equation

HRID 1386779 reaction equation
C(OP([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[CH2:19]([N:26]1[CH2:31][CH2:30][C:29](=O)[CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[CH2:19]([N:26]1[CH2:31][CH2:30][C:29](=[CH:9][C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 192201-Benzyl-4-piperidoneHCID 24758Sodium hydrideHCID 2773685tert-Butyl diethylphosphonoacetate

Product 1

HCID 131722813HCID 131722813, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1.68 g of t-butyl diethylphosphonoacetate in 5 mL of THF was added 400 mg of sodium hydride (60% dispersion in mineral oil) at 0° C. The reaction was warmed to rt and stirred at rt for 20 min. To the resulting solution was added a solution of 1.05 g of 1-benzyl-4-piperidone in 5 mL of THF. The solution was refluxed for 3 h and cooled to rt. After quenching with aqueous NH4Cl, the aqueous phase was extracted with EtOAc (3×). The combined organic phases were dried over MgSO4 and concentrated to give 1.05 g of the title compound as a oil, which was used for the next step without further purification.

Workup

  1. temperatureThe solution was refluxed for 3 h
  2. temperaturecooled to rt
  3. customAfter quenching with aqueous NH4Cl
  4. extractionthe aqueous phase was extracted with EtOAc (3×)
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e9d562723b62447ab2936d8292c294d7
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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