Methyl Methacrylate → 2-(1-Piperidinyl)ethyl 2-methyl-2-propenoate

HRID 648439Notes

Reaction equation

HRID 648439 reaction equation
[N:1]1([CH:7](O)[CH3:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[O-].[Na+].COC1C=CC(O)=CC=1.[C:22]([O:27]C)(=[O:26])[C:23]([CH3:25])=[CH2:24]>C(O)(=O)C>[C:22]([O:27][CH2:8][CH2:7][N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)(=[O:26])[C:23]([CH3:25])=[CH2:24]

Participants

6

Reactant 4

HCID 6658Methyl MethacrylateHCID 90154-MethoxyphenolHCID 30305411-(Piperidin-1-yl)ethanolHCID 10942334Sodium Methoxide

Product 1

HCID 5801832-(1-Piperidinyl)ethyl 2-methyl-2-propenoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 1 liter resin kettle was fitted with an air bubbler, temperature probe and still head. To the kettle was added, in order: 233 grams piperidinoethanol, 5.0 grams sodium methoxide, 0.5 grams p-methoxy phenol (to inhibit polymerization), and 750 milliliters methyl methacrylate. With a slow stream of air bubbling through the reaction mixture, the mixture was stirred vigorously and heated to 80 degrees with a constant temperature water bath. 5.0 grams sodium methoxide were added 30 and 60 minutes after the start of the reaction. After 120 minutes, the reaction mixture was cooled and neutralized with 17.0 grams acetic acid. The reaction mixture was transferred to a separatory funnel. The product was extracted from the reaction mixture into one liter of aqueous solution containing 95 grams concentrated sulfuric acid. The reaction mixture was treated with 500 milliliters of aqueous solution containing 15 grams concentrated sulfuric acid to extract remaining product. The two aqueous portions were combined and extracted with petroleum ether (boiling point 30-60 degrees) to remove residual methyl methacrylate, then rendered basic with 500 milliliters of aqueous solution containing 150 grams potassium hydroxide. The product was extracted from the aqueous solution with petroleum ether. The petroleum ether solution was dried over anhydrous magnesium sulfate. The petroleum ether was removed from the product with a rotary film evaporator under reduced pressure.

Workup

  1. additionTo the kettle was added, in order
  2. customWith a slow stream of air bubbling through the reaction mixture
  3. temperatureheated to 80 degrees with a constant temperature water bath
  4. addition5.0 grams sodium methoxide were added 30 and 60 minutes
  5. customafter the start of the reaction
  6. temperaturethe reaction mixture was cooled
  7. customThe reaction mixture was transferred to a separatory funnel
  8. extractionThe product was extracted from the reaction mixture into one liter of aqueous solution
  9. additioncontaining 95 grams concentrated sulfuric acid
  10. additionThe reaction mixture was treated with 500 milliliters of aqueous solution
  11. additioncontaining 15 grams concentrated sulfuric acid
  12. extractionto extract
  13. extractionextracted with petroleum ether (boiling point 30-60 degrees)
  14. customto remove residual methyl methacrylate
  15. additioncontaining 150 grams potassium hydroxide
  16. extractionThe product was extracted from the aqueous solution with petroleum ether
  17. dry with materialThe petroleum ether solution was dried over anhydrous magnesium sulfate
  18. customThe petroleum ether was removed from the product with a rotary film evaporator under reduced pressure

Sources & evidence

ORD record
ord-16fb39f0d69a4064853fe35cce48be2e
Source dataset
uspto-grants-1988_04
Patent number
US04735887

Reaction notes

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