Acetic Anhydride → HCID 20446377, compound

HRID 2418459Notes

Reaction equation

HRID 2418459 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:7][CH:6]([N:8]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]2=[O:15])[CH2:5][C:4]([CH3:17])([CH3:16])[NH:3]1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>S(=O)(=O)(O)O>[C:19]([N:3]1[C:4]([CH3:17])([CH3:16])[CH2:5][CH:6]([N:8]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]2=[O:15])[CH2:7][C:2]1([CH3:18])[CH3:1])(=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 185514351-(2,2,6,6-Tetramethylpiperidin-4-yl)azepan-2-one

Product 1

HCID 20446377HCID 20446377, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
120 °C

Procedure

A solution of 50.5 g (0.2 mole) of N-(2,2,6,6-tetramethylpiperidin-4-yl)-epsilon-caprolactam, prepared in Example 1, in 102 g of acetic anhydride with 0.2 g of sulfuric acid catalyst is heated for four hours at 120° C. At the end of this period the excess acetic anhydride is removed in vacuo. The residue is then dissolved in 200 ml of methylene chloride, washed thrice with 100 ml portions of water, then with 10% aqueous sodium bicarbonate and finally dried over anhydrous magnesium sulfate. The solvent is allowed to evaporate to give a crude product which when recrystallized from toluene:hexane (1:3) yields 38.4 g of white solid melting at 104°-108° C.

Workup

  1. customAt the end of this period the excess acetic anhydride is removed in vacuo
  2. dissolutionThe residue is then dissolved in 200 ml of methylene chloride
  3. washwashed thrice with 100 ml portions of water
  4. dry with materialwith 10% aqueous sodium bicarbonate and finally dried over anhydrous magnesium sulfate
  5. customto evaporate
  6. customto give a crude product which when
  7. customrecrystallized from toluene:hexane (1:3)

Sources & evidence

ORD record
ord-13be9dd6a81b4345a7b784cb112fbd16
Source dataset
uspto-grants-1984_09
Patent number
US04472547

Reaction notes

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