ethyl N-(2,2,6,6-tetramethyl-4-piperidinyl)oxamate → HCID 20085781, compound

HRID 1608872Notes

Reaction equation

HRID 1608872 reaction equation
[C:1]([O:5][CH2:6][CH:7]=[CH2:8])(=[O:4])[NH:2][NH2:3].[CH3:9][C:10]1([CH3:26])[CH2:15][CH:14]([NH:16][C:17](=[O:23])[C:18](OCC)=[O:19])[CH2:13][C:12]([CH3:25])([CH3:24])[NH:11]1>CO>[CH3:9][C:10]1([CH3:26])[CH2:15][CH:14]([NH:16][C:17](=[O:23])[C:18]([NH:3][NH:2][C:1]([O:5][CH2:6][CH:7]=[CH2:8])=[O:4])=[O:19])[CH2:13][C:12]([CH3:25])([CH3:24])[NH:11]1

Participants

4

Reactant 2

HCID 11118680ethyl N-(2,2,6,6-tetramethyl-4-piperidinyl)oxamateHCID 11137137Hydrazinecarboxylic acid, 2-propenyl ester

Product 1

HCID 20085781HCID 20085781, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Into a 250 ml 3-neck flask was added 9.2 grams (0,079 mole) of allyl carbazate from (A), 34.2 grams (0.08 mole) of a 60% solution of ethyl N-(2,2,6,6-tetramethyl-4-piperidinyl)oxamate and 50 ml of methanol. The flask was equipped with a magnetic stirrer, thermometer and a Dean Stark trap with a reflux The reaction was heated in an oil bath and the methanol was distilled off through the Dean Stark trap. After the methanol distillation ceased, a vacuum was applied to the system to remove any residual methanol and the reaction was cooked for 80 minutes at 90° C. The reaction was cooled to 50° C. and 50 ml of methanol was added and the reaction heated back up to reflux to dissolve the residue. The methanol solution was cooled and concentrated to 25 ml. Upon addition of 25 ml of methyl t-butyl ether, a white solid formed. The solid was filtered off and dried in a vacuum oven over night. The dry powder weighed 22.1 grams (85.7% yield) and assayed 100% by liquid chromatography. The infrared scan of the product contained a weak carbonyl at 1750 cm-1 and a strong carbonyl at 1680 cm-1.

Workup

  1. customThe flask was equipped with a magnetic stirrer
  2. temperaturethermometer and a Dean Stark trap with a reflux The reaction
  3. temperaturewas heated in an oil bath
  4. distillationthe methanol was distilled off through the Dean Stark trap
  5. distillationAfter the methanol distillation
  6. customto remove any residual methanol
  7. addition50 ml of methanol was added
  8. temperaturethe reaction heated back up
  9. temperatureto reflux
  10. dissolutionto dissolve the residue
  11. temperatureThe methanol solution was cooled
  12. concentrationconcentrated to 25 ml
  13. additionUpon addition of 25 ml of methyl t-butyl ether
  14. customa white solid formed
  15. filtrationThe solid was filtered off
  16. customdried in a vacuum oven over night

Sources & evidence

ORD record
ord-72118b43b40a479eaf49be832c95c49f
Source dataset
uspto-grants-1995_03
Patent number
US05397821

Reaction notes

Loading…