Piperidine → 1-Phenyl-2-(piperidin-1-yl)ethane-1,2-dione

HRID 891225Notes

Reaction equation

HRID 891225 reaction equation
[C:1]1([C:7](=[O:12])[C:8]([O:10]C)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>CO>[C:1]1([C:7](=[O:12])[C:8]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 84835Methyl phenylglyoxalate

Product 1

HCID 109659651-Phenyl-2-(piperidin-1-yl)ethane-1,2-dioneYield 96.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl phenylglyoxylate (12.50 Kg, 76.1 mol, 1 eq) was added dropwise to a stirred mixture of piperidine (19.45 Kg, 228 mol, 3 eq) and methanol (5.0 L) for 3.5 hours to maintain the temperature at 45–55° C. The mixture was stirred at the same temperature for 0.5 hour and kept overnight at +4° C. The precipitated solid was filtered off, washed on the filter with cold methanol (5 L) and dried under reduced pressure to a constant weight to give 15.90 kg (96%) of 1-(phenylglyoxylyl)piperidine with 99.9% purity by GC.

Workup

  1. temperatureto maintain the temperature at 45–55° C
  2. waitkept overnight at +4° C
  3. filtrationThe precipitated solid was filtered off
  4. washwashed on the
  5. filtrationfilter with cold methanol (5 L)
  6. customdried under reduced pressure to a constant weight

Sources & evidence

ORD record
ord-0cef45f09e524e45baaa43f69dbefd50
Source dataset
uspto-grants-2006_02
Patent number
US07002016B2

Reaction notes

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