1-Benzyl-4-piperidone → HCID 59993160, compound

HRID 238234Notes

Reaction equation

HRID 238234 reaction equation
[H-].[Na+].C(OP([CH:11]([CH3:16])[C:12]([O:14][CH3:15])=[O:13])(OCC)=O)C.[CH2:17]([N:24]1[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[CH3:15][O:14][C:12](=[O:13])[C:11](=[C:27]1[CH2:28][CH2:29][N:24]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:25][CH2:26]1)[CH3:16]

Participants

5

Reactant 3

HCID 192201-Benzyl-4-piperidoneHCID 24758Sodium hydrideHCID 11401826methyl 2-(diethoxyphosphoryl)-propionate

Product 1

HCID 59993160HCID 59993160, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of NaH (60% in mineral oil, 6 g, 0.15 mol) in dry THF (300 mL), under N2 atmosphere, was added a solution of methyl 2-(diethoxyphosphoryl)-propionate (33.6 g, 0.15 mol) in dry THF (150 mL) at such a rate to keep the temperature below 30° C. After being stirred at r.t for 40 min, a solution of N-benzyl-4-piperidone (28.35 g, 0.15 mol) in dry THF (100 mL) was added dropwise keeping the temperature below 30° C. After the addition was completed, the mixture was stirred at r.t for 30 min. The reaction was quenched with NH4Cl (sat. aq., 400 mL). The mixture was extracted with Et2O (300 mL×2) and the combined extracts were washed with brine, dried and concentrated to give the crude product as a red oil, which was used directly in the next step.

Workup

  1. customthe temperature below 30° C
  2. customthe temperature below 30° C
  3. additionAfter the addition
  4. stirringthe mixture was stirred at r.t for 30 min
  5. customThe reaction was quenched with NH4Cl (sat. aq., 400 mL)
  6. extractionThe mixture was extracted with Et2O (300 mL×2)
  7. washthe combined extracts were washed with brine
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-474ebe5d999743cbbd2dceac18a431c9
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

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