Formaldehyde → HCID 19784656, compound

HRID 2082447Notes

Reaction equation

HRID 2082447 reaction equation
[CH2:1]([CH:8]1[CH:13]([OH:14])[CH2:12][C:11]([CH3:16])([CH3:15])[NH:10][C:9]1([CH3:18])[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]=O.[OH-].[Na+]>O1CCOCC1>[CH2:1]([CH:8]1[CH:13]([OH:14])[CH2:12][C:11]([CH3:16])([CH3:15])[N:10]([CH3:19])[C:9]1([CH3:18])[CH3:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 19094733HCID 19094733, compound

Product 1

HCID 19784656HCID 19784656, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
80 °C

Procedure

Into a 100 ml-flask equipped with a thermometer, a cooling tube, a dropping funnel and a magnetic stirrer were added 3.7 g of 3-benzyl-2,2,6,6-tetramethyl-4-piperidinol prepared in Example A1 above, 30 ml of dioxane and 0.78 g of fumic acid, and the content in the flask was heated to 80° C. When the temperature of the content was at a constant level, 2.44 g of 37% aqueous formaldehyde in which 10 ml of dioxane had been dissolved was introduced gradually through the dropping funnel, and the content of the flask was heated at the same temperature under agitation for 8 hours. The temperature was then lowered to room temperature, 10% aqueous NaOH was added so that the pH became to 7, and the solution was subjected to extraction with 150 ml of diethylether. The extract obtained was washed three times with 30 ml of water, 10 g of magnesium sulfate and the solution was kept standing for 2 hours, and the solution was filtered and concentrated to give 3.3 g (yield: 83%) of the title compound as a white solid product.

Workup

  1. customInto a 100 ml-flask equipped with a thermometer, a cooling tube, a dropping funnel and a magnetic stirrer
  2. dissolutionhad been dissolved
  3. additionwas introduced gradually through the dropping funnel
  4. temperaturethe content of the flask was heated at the same temperature under agitation for 8 hours
  5. customwas then lowered to room temperature
  6. extractionthe solution was subjected to extraction with 150 ml of diethylether
  7. customThe extract obtained
  8. washwas washed three times with 30 ml of water, 10 g of magnesium sulfate
  9. filtrationthe solution was filtered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-918647968a0c40b0ac34da6bdc0547ee
Source dataset
uspto-grants-1993_02
Patent number
US05189172

Reaction notes

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