Methacrylic Acid → HCID 15375485, compound

HRID 743635Notes

Reaction equation

HRID 743635 reaction equation
[NH2:1][CH:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[NH:5][C:4]([CH3:11])([CH3:10])[CH2:3]1.[C:12]([OH:17])(=O)[C:13]([CH3:15])=[CH2:14]>>[CH3:14][CH:13]([CH2:15][NH:1][CH:2]1[CH2:3][C:4]([CH3:11])([CH3:10])[NH:5][C:6]([CH3:9])([CH3:8])[CH2:7]1)[C:12]([NH:1][CH:2]1[CH2:3][C:4]([CH3:11])([CH3:10])[NH:5][C:6]([CH3:9])([CH3:8])[CH2:7]1)=[O:17]

Participants

3

Reactant 2

HCID 4093Methacrylic AcidHCID 375244-Amino-2,2,6,6-tetramethylpiperidine

Product 1

HCID 15375485HCID 15375485, compoundYield 55.4%

Conditions

Temperature
145 °C

Procedure

Into a 3 liter flask, 1560 g of 4-amino-2,2,6,6-tetramethylpiperidine was placed. After the temperature was raised to 145° C., 430 g of methacrylic acid was added dropwise thereto. The inner temperature rose gradually and then the reaction mixture was kept at 170°±5° C., while collecting water distilled off, until the water collected had amounted to 90 g. Then the reaction mixture was cooled down to 50° C., and 500 g of acetone was added to the mixture to obtain a light yellowish slurry. The slurry thus obtained was cooled down to 20° C. and filtered. The filter cake was washed with acetone and dried to obtain 1053 g of pure white 2-methyl-3-(2,2,6,6-tetramethyl-4-piperidylamino)-N-(2,2,6,6-tetramethyl-4-piperidyl)propionamide (hereinafter referred to as Compound 1). M.p.: 115.5°-116.5° C. Mass spectrometry (FD-MS): m/z 380 (M+).

Workup

  1. customwas kept at 170°±5° C.
  2. customwhile collecting water
  3. distillationdistilled off, until the water
  4. customcollected
  5. temperatureThen the reaction mixture was cooled down to 50° C.
  6. addition500 g of acetone was added to the mixture
  7. customto obtain a light yellowish slurry
  8. customThe slurry thus obtained
  9. temperaturewas cooled down to 20° C.
  10. filtrationfiltered
  11. washThe filter cake was washed with acetone
  12. customdried

Sources & evidence

ORD record
ord-328b74d09dc74baeaf93f1a181d533d1
Source dataset
uspto-grants-1996_09
Patent number
US05556980

Reaction notes

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