Formaldehyde → HCID 19010880, compound

HRID 1741772Notes

Reaction equation

HRID 1741772 reaction equation
[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][NH:11][C:10](=[O:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:20].[Na+].[CH2:22]=O>C(O)C.O>[OH:20][CH2:22][N:11]1[CH2:12][C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9][C:10]1=[O:13]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 19010883HCID 19010883, compound

Product 1

HCID 19010880HCID 19010880, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred mixture of 37 g (0.147 mol) of 5,5 diphenyl-2-piperidinone and 24 g of sodium hydroxide in 170 mL of ethanol at ambient temperature was added dropwise 165 mL of a 35-40% formaldehyde in water solution during 10 minutes. The mixture was heated at reflux temperature overnight, concentrated to near dryness and partitioned between ethyl acetate and water. The organic layer was washed with water and brine, and dried. Concentration at less than 30° C. under vacuum, trituration with hexanes and filtration gave 28 g of product, mp 140°-150° C.(decomp.).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature overnight
  3. concentrationconcentrated
  4. custompartitioned between ethyl acetate and water
  5. washThe organic layer was washed with water and brine
  6. customdried
  7. concentrationConcentration at less than 30° C. under vacuum, trituration
  8. filtrationwith hexanes and filtration

Sources & evidence

ORD record
ord-0e39d2446fea4abd86c36d69a7bbe13f
Source dataset
uspto-grants-1994_08
Patent number
US05334720

Reaction notes

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