Oxygen → HCID 23052601, compound

HRID 1650873Notes

Reaction equation

HRID 1650873 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:7][CH:6]([NH2:8])[CH2:5][C:4]([CH3:10])([CH3:9])[NH:3]1.[C:12]([O:16][O:17][C:18](=[O:24])[CH2:19][CH2:20][C:21](Cl)=[O:22])([CH3:15])([CH3:14])[CH3:13].C(OOC(=O)CCC(O)=O)(C)(C)C.O=O>C(Cl)Cl>[CH3:1][C:2]1([CH3:11])[CH2:7][CH:6]([NH:8][C:21](=[O:22])[CH2:20][CH2:19][C:18]([O:17][O:16][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:24])[CH2:5][C:4]([CH3:10])([CH3:9])[NH:3]1

Participants

6

Reactant 4

HCID 977OxygenHCID 375244-Amino-2,2,6,6-tetramethylpiperidineHCID 12329418tert-Butyl 4-chloro-4-oxobutaneperoxoateHCID 12590030HCID 12590030, compound

Product 1

HCID 23052601HCID 23052601, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
30 °C

Procedure

Into a 250 ml flask equipped with a magnetic stirrer, thermometer, condenser, addition funnel and calcium chloride drying tube were placed 2,2,6,6-tetramethyl-4-aminopiperidine (20.3 g, 0.13 mole) and 50 ml of methylene chloride. The addition funnel was charged with 4-t-butylperoxy-4-oxobutanoyl chloride (13.2 g, 0.06 mole) and 50 ml methylene chloride. The acid chloride was added dropwise at 20°-23° C. over a 20 minute period, causing a slight exotherm. The reaction mixture was warmed to 30° C. over 60 minutes and then stirred at 30° C. for another 30 minutes. The reaction mixture was poured into a jacketed reactor and washed at 20°-25° C. with eight 50 ml portions of water. The organic material was dried with anhydrous magnesium sulfate and the solvent stripped under reduced pressure to give 9.3 g of a light amber-straw liquid. Liquid chromatography of this product showed it to contain two components, one of which was 4-t-butylperoxy-4-oxobutanoic acid. Iodometric analysis indicated 5.65% active oxygen content which corresponds to a mixture of 22% perester-acid and 78% perester-amide (C-VII). The infrared spectrum (neat) showed three carbonyl absorptions at 1650, 1700 and 1770 cm-1 (amide, acid and perester) and a broad absorption at 3300 cm-1. Based on the 78% assay, the product was prepared in 37% corrected yield.

Workup

  1. customInto a 250 ml flask equipped with a magnetic stirrer
  2. additionthermometer, condenser, addition funnel and calcium chloride drying tube
  3. additionThe reaction mixture was poured into a jacketed reactor
  4. washwashed at 20°-25° C. with eight 50 ml portions of water
  5. dry with materialThe organic material was dried with anhydrous magnesium sulfate
  6. customto give 9.3 g of a light amber-straw liquid
  7. additioncorresponds to a mixture of 22% perester-acid
  8. customa broad absorption at 3300 cm-1
  9. customthe product was prepared in 37%
  10. customcorrected yield

Sources & evidence

ORD record
ord-fd6189e216a54c4882929579e8cd657a
Source dataset
uspto-grants-1990_05
Patent number
US04925903

Reaction notes

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