Hydrazine → 1,2,2,6,6-Pentamethyl-4-piperidinyl Carbazate

HRID 1742467Notes

Reaction equation

HRID 1742467 reaction equation
[C:1](=O)([O:9][CH:10]1[CH2:15][C:14]([CH3:17])([CH3:16])[N:13]([CH3:18])[C:12]([CH3:20])([CH3:19])[CH2:11]1)[O:2]C1C=CC=CC=1.[NH2:22][NH2:23]>CO>[C:1]([O:9][CH:10]1[CH2:15][C:14]([CH3:17])([CH3:16])[N:13]([CH3:18])[C:12]([CH3:20])([CH3:19])[CH2:11]1)(=[O:2])[NH:22][NH2:23]

Participants

4

Reactant 2

HCID 9321Hydrazine2×HCID 20085740Phenyl 1,2,2,6,6-Pentamethyl-4-piperidinyl Carbonate

Product 1

HCID 538648061,2,2,6,6-Pentamethyl-4-piperidinyl Carbazate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Into a 250 ml 3-neck flask was added 20.0 grams (0.069 mole) of phenyl 1,2,2,6,6-pentamethyl-4-piperidinyl carbonate and 100 mls of methanol. The flask was equipped with a magnetic stirrer, thermometer, reflux condenser and dropping funnel containing 3.8 grams (0.076 mole) of 64% aqueous hydrazine. The hydrazine was added slowly to the stirring methanol solution at room temperature. There was a slight exotherm. The reaction mixture was stirred for 5 hours at room temperature at which point liquid chromatography indicated the reaction was complete. The methanol was stripped off on a rotating evaporator under reduced pressure and the residue was dissolved in 150 ml MtBE. The MtBE solution was washed 3 times with 25 ml portions of 5% NaOH saturated with sodium chloride to remove the phenol that was generated. The MtBE layer was dried over anhydrous MgSO4, filtered and the MtBE stripped off on a rotating evaporator under reduced pressure. The residue was a white solid (m.p. 90°-94° C.) weighing 14.3 grams (90.5% crude yield). Liquid chromatography indicated the product was one component. The infrared spectrum contained a strong carbonyl peak at 1710 cm-1 and a moderate peak at 1625 cm-1.

Workup

  1. customThe flask was equipped with a magnetic stirrer
  2. temperaturethermometer, reflux condenser
  3. customThe methanol was stripped off on a rotating evaporator under reduced pressure
  4. dissolutionthe residue was dissolved in 150 ml MtBE
  5. washThe MtBE solution was washed 3 times with 25 ml portions of 5% NaOH saturated with sodium chloride
  6. customto remove the phenol that
  7. dry with materialThe MtBE layer was dried over anhydrous MgSO4
  8. filtrationfiltered
  9. customthe MtBE stripped off on a rotating evaporator under reduced pressure

Sources & evidence

ORD record
ord-283e5a5e9bff4afeae833f80bf3c607c
Source dataset
uspto-grants-1994_08
Patent number
US05338853

Reaction notes

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