ethyl N-(2,2,6,6-tetramethyl-4-piperidinyl)oxamate → 1-[N-(2,2,6,6-tetramethyl-4-piperidinyl)oxamoyl]-2-[N-(2,2,6,6-tetramethyl-4-piperidinyl)succinamoyl]hydrazine

HRID 1742464Notes

Reaction equation

HRID 1742464 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:7][CH:6]([NH:8][C:9](=[O:15])[C:10]([O:12]CC)=O)[CH2:5][C:4]([CH3:17])([CH3:16])[NH:3]1.[CH3:19][C:20]1([CH3:37])[CH2:25][CH:24]([NH:26][C:27](=[O:34])[CH2:28][CH2:29][C:30]([NH:32][NH2:33])=[O:31])[CH2:23][C:22]([CH3:36])([CH3:35])[NH:21]1>CO>[CH3:18][C:2]1([CH3:1])[CH2:7][CH:6]([NH:8][C:9](=[O:15])[C:10]([NH:33][NH:32][C:30](=[O:31])[CH2:29][CH2:28][C:27]([NH:26][CH:24]2[CH2:23][C:22]([CH3:35])([CH3:36])[NH:21][C:20]([CH3:37])([CH3:19])[CH2:25]2)=[O:34])=[O:12])[CH2:5][C:4]([CH3:16])([CH3:17])[NH:3]1

Participants

4

Reactant 2

HCID 11118680ethyl N-(2,2,6,6-tetramethyl-4-piperidinyl)oxamateHCID 14745323N-(2,2,6,6-tetramethyl-4-piperidinyl)-N'-aminosuccinamide

Product 1

HCID 200857791-[N-(2,2,6,6-tetramethyl-4-piperidinyl)oxamoyl]-2-[N-(2,2,6,6-tetramethyl-4-piperidinyl)succinamoyl]hydrazine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Into a 3-necked 50 ml flask was introduced a 60.9% solution of ethyl N-(2,2,6,6-tetramethyl-4-piperidinyl)oxamate in methanol (4.27 g, 0.01 mole), N-(2,2,6,6-tetramethyl-4-piperidinyl)-N'-aminosuccinamide (2.7 g, 0.01 mole) and 25 ml of anhydrous methanol. The flask was equipped with a thermometer, a magnetic stirrer and a Dean Stark trap with a reflux condenser. The reaction mixture was heated to reflux for 1/2 hour. Liquid chromatography of the reaction mixture indicated that the starting materials had essentially disappeared and there was one new peak corresponding to the product. The reaction mixture was filtered hot to remove some insoluble material. The filtrate was stripped to dryness on a rotatary evaporator under reduced pressure. The residue was scraped out of the flask and pulverized into a white powder with a mortar and pestle. The white powder was air dried on a watch glass overnight. The product weighed 1.0 grams and had a melting range of 130°-135° C. An infrared scan (nujol mull) of the product contained a strong carbonyl band at 1655 cm-1 and two moderate carbonyl bands at 1575 and 1495 cm-1.

Workup

  1. customThe flask was equipped with a thermometer, a magnetic stirrer
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 1/2 hour
  4. filtrationThe reaction mixture was filtered hot
  5. customto remove some insoluble material
  6. customThe filtrate was stripped to dryness on a rotatary evaporator under reduced pressure
  7. customdried on a watch glass overnight

Sources & evidence

ORD record
ord-1e08451b5a1340189849ebd2d8b3b6fd
Source dataset
uspto-grants-1994_08
Patent number
US05338853

Reaction notes

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