Formic Acid → HCID 19784640, compound

HRID 257154Notes

Reaction equation

HRID 257154 reaction equation
[CH:1]1([CH2:7][CH:8]2[CH:13]([OH:14])[CH2:12][C:11]([CH3:16])([CH3:15])[NH:10][C:9]2([CH3:18])[CH3:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:19](O)=O.C=O.[OH-].[Na+]>O1CCOCC1>[CH:1]1([CH2:7][CH:8]2[CH:13]([OH:14])[CH2:12][C:11]([CH3:16])([CH3:15])[N:10]([CH3:19])[C:9]2([CH3:18])[CH3:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 19784639HCID 19784639, compound

Product 1

HCID 19784640HCID 19784640, compoundYield 98.5%

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 introduced 3.8 g (15 mmol) of 3-cyclohexylmethyl-2,2,6,6-tetramethyl-4-piperidinol prepared in Example B1, 70 ml of dioxane and 0.78 g (17 mmol) of formic acid, and the content of the flask was heated to 80° C. When the temperature of the content of the flask was constant, 2.44 g (30 mmol) of 37% aqueous formaldehyde dissolved in 20 ml of dioxane was added gradually through the dropping funnel, followed by heating at the temperature for 10 hours. The content of the flask was cooled to room temperature, and 5% aqueous NaOH was added so that the pH became 8, followed by extraction with 200 ml of diethylether. The extract obtained was washed with 30 ml of water 3 times, 10 g of magnesium sulfate was added and, after it was kept standing for ca. 2 hours, the solution was filtered and concentrated to give 3.95 g (yield: 98%) 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. additionwas added gradually through the dropping funnel
  3. temperatureby heating at the temperature for 10 hours
  4. temperatureThe content of the flask was cooled to room temperature
  5. extractionfollowed by extraction with 200 ml of diethylether
  6. customThe extract obtained
  7. washwas washed with 30 ml of water 3 times, 10 g of magnesium sulfate
  8. additionwas added
  9. filtrationthe solution was filtered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-a58843332b3b4da5b05082d89b70e4b5
Source dataset
uspto-grants-1993_11
Patent number
US05260443

Reaction notes

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