Triethylamine → HCID 23052607, compound

HRID 1650872Notes

Reaction equation

HRID 1650872 reaction equation
[CH3:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([OH:10])[CH2:4][C:3]1([CH3:12])[CH3:11].C(N(CC)CC)C.[C:20]([O:24][O:25][C:26](=[O:32])[CH2:27][CH2:28][C:29](Cl)=[O:30])([CH3:23])([CH3:22])[CH3:21].[OH-].[Na+]>CCCCC.C(OC)(C)(C)C>[CH3:1][N:2]1[C:7]([CH3:8])([CH3:9])[CH2:6][CH:5]([O:10][C:29](=[O:30])[CH2:28][CH2:27][C:26]([O:25][O:24][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:32])[CH2:4][C:3]1([CH3:12])[CH3:11]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 754724-Piperidinol, 1,2,2,6,6-pentamethyl-HCID 12329418tert-Butyl 4-chloro-4-oxobutaneperoxoate

Product 1

HCID 23052607HCID 23052607, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 8003PentaneSolvent3×HCID 15413tert-Butyl methyl etherSolvent2×

Procedure

Into a 500 ml flask equipped with a magnetic stirbar, thermometer, addition funnel, and nitrogen atmosphere sparger were placed 7.6 g (0.044 mole) of 1,2,2,6,6-pentamethyl-4-piperidinol, 4.4 g (0.044 mole) of triethylamine, and 100 ml of pentane. The addition funnel was charged with 9.7 g (0.044 mole) of 4-t-butylperoxy-4-oxobutanoyl chloride, 50 ml of methyl t-butyl ether and 50 ml of pentane. The acid chloride was added dropwise to the reaction mixture at a rate maintaining the temperature of the reaction less than 27° C. (about 70 min. for complete addition). After this addition, the reaction mixture was allowed to stir at ambient temperature for 45 minutes. To the mixture 100 ml of 5% aqueous sodium hydroxide (chilled to 5° C.) was then added with rapid stirring. The mixture was transferred to a separatory funnel with 100 ml of methyl t-butyl ether and 100 ml of pentane. The funnel was shaken and allowed to separate; and the aqueous phase was drawn off. The organic phase was extracted with 100 ml of aqueous 5% sodium hydroxide (chilled to 5° C.), and twice with 100 ml portions of cold (5° C.) water. The organic solution was dried with anhydrous sodium sulfate and the solvent was stripped using aspirator and high vacuum systems. The residue was transferred to a flask with 30 ml of pentane and treated with 5.3 g of decolorizing carbon (occasional swirling for 90 minutes). The mixture was diluted with 200 ml of pentane, filtered free from carbon, and stripped of solvent using aspirator and high vacuum. The product was a yellow oil weighing 9.7 g. Analysis showed an assay of 96.1% and corrected yield of 62.2%.

Workup

  1. customInto a 500 ml flask equipped with a magnetic stirbar
  2. additionthermometer, addition funnel
  3. temperaturemaintaining
  4. customthe temperature of the reaction less than 27° C. (about 70 min. for complete addition)
  5. additionAfter this addition
  6. stirringThe funnel was shaken
  7. customto separate
  8. extractionThe organic phase was extracted with 100 ml of aqueous 5% sodium hydroxide (chilled to 5° C.)
  9. customtwice with 100 ml portions of cold (5° C.) water
  10. dry with materialThe organic solution was dried with anhydrous sodium sulfate
  11. customThe residue was transferred to a flask with 30 ml of pentane
  12. additiontreated with 5.3 g of decolorizing carbon (occasional swirling for 90 minutes)
  13. additionThe mixture was diluted with 200 ml of pentane
  14. filtrationfiltered free from carbon

Sources & evidence

ORD record
ord-1e42c6281e554414a936f7b05a9e5f75
Source dataset
uspto-grants-1990_05
Patent number
US04925903

Reaction notes

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