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

HRID 1296785Notes

Reaction equation

HRID 1296785 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

Conditions

Temperature
50 °C

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

Sources & evidence

ORD record
ord-dba5c389dc124ccc8f97f7c42cac75e0
Source dataset
uspto-grants-2007_07
Patent number
US07247730B2

Reaction notes

Loading…