Hydrazine → HCID 21620560, compound

HRID 1742470Notes

Reaction equation

HRID 1742470 reaction equation
[C:1](=O)([O:9][CH:10]1[CH2:15][C:14]([CH3:17])([CH3:16])[NH:13][C:12]([CH3:19])([CH3:18])[CH2:11]1)[O:2]C1C=CC=CC=1.[NH2:21][NH2:22]>CO>[C:1]([O:9][CH:10]1[CH2:15][C:14]([CH3:17])([CH3:16])[NH:13][C:12]([CH3:19])([CH3:18])[CH2:11]1)(=[O:2])[NH:21][NH2:22]

Participants

4

Reactant 2

HCID 9321Hydrazine2×HCID 54363423HCID 54363423, compound

Product 1

HCID 21620560HCID 21620560, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Into a 300 ml 3-neck flask were added 16.9 grams (0.061 mole) of phenyl 2,2,6,6-tetramethyl-4-piperidinyl carbonate and 100 ml of methanol. The flask was equipped with a magnetic stirrer, thermometer, reflux condenser and dropping funnel containing 3.4 grams (0.067 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 3 hours and then allowed to stand overnight (i.e. for 20 hours) at room temperature. The next day, the methanol was stripped off on a rotating evaporator and the liquid residue dissolved in 150 ml of MtBE and washed with 50 ml of 10% NaOH which was saturated with salt. The MtBE solution was dried over anhydrous MgSO4, filtered and the MtBE stripped off on a rotating evaporator under reduced pressure. The residue, a very viscous liquid, was slurried in 20 ml of hexane until a solid formed. The solid was filtered off and air dried. The product weighed 6.4 grams (49% crude yield), had a melting point of 93°-94° C. and gas chromatography indicated it was about 95% pure. The infrared scan contained a strong carbonyl peak at 1710 cm-1 and a moderate carbonyl peak at 1625 cm-1. An additional 5.26 grams of crude product was recovered by extracting the aqueous wash with methylene chloride and stripping off the solvent.

Workup

  1. customThe flask was equipped with a magnetic stirrer
  2. temperaturethermometer, reflux condenser
  3. waitto stand overnight
  4. custom(i.e. for 20 hours)
  5. customat room temperature
  6. customThe next day, the methanol was stripped off on a rotating evaporator
  7. dissolutionthe liquid residue dissolved in 150 ml of MtBE
  8. washwashed with 50 ml of 10% NaOH which
  9. dry with materialThe MtBE solution was dried over anhydrous MgSO4
  10. filtrationfiltered
  11. customthe MtBE stripped off on a rotating evaporator under reduced pressure
  12. customformed
  13. filtrationThe solid was filtered off
  14. customair dried
  15. customAn additional 5.26 grams of crude product was recovered
  16. extractionby extracting the
  17. washaqueous wash with methylene chloride

Sources & evidence

ORD record
ord-c89e0761cb1f430781e180f53bec523c
Source dataset
uspto-grants-1994_08
Patent number
US05338853

Reaction notes

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