Acetic Acid → N-(2-cycloheptenyl)succinimide

HRID 247619Notes

Reaction equation

HRID 247619 reaction equation
[CH:1]1([NH2:8])[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[C:9]1(=O)[O:14][C:12](=[O:13])[CH2:11][CH2:10]1.C(O)(=O)C>CCOCC>[CH:1]1([N:8]2[C:12](=[O:13])[CH2:11][CH2:10][C:9]2=[O:14])[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7922Succinic anhydrideHCID 11263481Cyclohept-2-en-1-amine

Product 1

HCID 13506505N-(2-cycloheptenyl)succinimideYield 61%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-cycloheptenylamine (1.01 g), succinic anhydride (1.0 g) and acetic acid (10 ml) was heated under reflux for 24 hours. After cooling, ether (20 ml) was added to the reaction mixture which was then washed with a saturated aqueous sodium hydrogencarbonate solution, water and a saturated aqueous sodium chloride solution in this order. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The oily product thus obtained was purified by column chromatography on silica gel to obtain 1.07 g of N-(2-cycloheptenyl)succinimide [Compound (214)].

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. temperatureAfter cooling
  4. washwas then washed with a saturated aqueous sodium hydrogencarbonate solution, water
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe oily product thus obtained
  8. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d85c1bd7d8ad41a89dce0a9b4c209136
Source dataset
uspto-grants-1987_11
Patent number
US04709052

Reaction notes

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