Acetic Anhydride → HCID 21498552, compound

HRID 1729967Notes

Reaction equation

HRID 1729967 reaction equation
[CH3:1][C:2]12[CH2:10][CH2:9][CH:5]([CH:6]([OH:8])[CH2:7]1)[C:4]([CH3:12])([CH3:11])[NH:3]2.[C:13](OC(=O)C)(=[O:15])[CH3:14]>C(O)(=O)C>[C:13]([O:8][CH:6]1[CH2:7][C:2]2([CH3:1])[CH2:10][CH2:9][CH:5]1[C:4]([CH3:12])([CH3:11])[NH:3]2)(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 214985461,3,3-Trimethyl-2-azabicyclo[2.2.2]octan-5-ol

Product 1

HCID 21498552HCID 21498552, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1.8 g (0.016 moles) of 1,3,3-trimethyl-2-azabicyclo[2.2.2]octane-5ol in 30 ml of glacial acetic acid in a 100 ml flask equipped with a magnetic stirrer, thermometer, condenser, and drying tube was added 1.0 ml (0.106 moles) of acetic anhydride. The solution was boiled under reflux for 20 hours. The reaction mixture was then cooled and evaporated under reduced pressure. The residue was taken up in hexane, and allowed to stand at room temperature overnight. The solution was then filtered and the filtrate evaporated under reduced pressure and dried under vacuum at 35° C, yielding 1.23 g of the desired material as a colorless oil.

Workup

  1. customthermometer, condenser, and drying tube
  2. temperatureunder reflux for 20 hours
  3. temperatureThe reaction mixture was then cooled
  4. customevaporated under reduced pressure
  5. filtrationThe solution was then filtered
  6. customthe filtrate evaporated under reduced pressure
  7. customdried under vacuum at 35° C

Sources & evidence

ORD record
ord-766a183fd5d74534b206f9f38d3b7579
Source dataset
uspto-grants-1976_11
Patent number
US03991012

Reaction notes

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