Formaldehyde → HCID 15487623, compound

HRID 367032Notes

Reaction equation

HRID 367032 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([OH:16])=[C:9]2[C:14]=1[NH:13][C:12](=[O:15])[CH2:11][CH2:10]2)[CH:2]=[CH2:3].[NH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[CH2:23]=O>C(O)C>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:23][N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[C:8]([OH:16])=[C:9]2[C:14]=1[NH:13][C:12](=[O:15])[CH2:11][CH2:10]2)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8082PiperidineHCID 12751739HCID 12751739, compound

Product 1

HCID 15487623HCID 15487623, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

41 Grams of 8-allyloxy-3,4-dihydro-5-hydroxy-2(1H)-quinolinone was dissolved in 500 ml of ethanol, under stirring 30 ml of piperidine and 30 ml of 37%-formalin were added to this solution, this mixture was stirred at 70° C. for 4 hours. After cooled, the reaction mixture was concentrated to dryness, extracted with 1 liter of methylene chloride, the extract was washed with water and dried, again concentrated to dryness. The residue was purified by a silica gel column chromatography (eluent: methylene chloride: ethyl acetate=20:1). The purified product was recrystallized from ethyl acetate, there was obtained 61g of 8-allyloxy-3,4-dihydro-5-hydroxy-6-(1-piperidinyl)methyl-2(1H)-quinolinone.

Workup

  1. additionwere added to this solution
  2. temperatureAfter cooled
  3. concentrationthe reaction mixture was concentrated to dryness
  4. extractionextracted with 1 liter of methylene chloride
  5. washthe extract was washed with water
  6. customdried
  7. concentrationagain concentrated to dryness
  8. customThe residue was purified by a silica gel column chromatography (eluent: methylene chloride: ethyl acetate=20:1)
  9. customThe purified product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9f582814bad6479fbb33fae86153c989
Source dataset
uspto-grants-2000_10
Patent number
US06133264

Reaction notes

Loading…