Toluene → 2-Azabicyclo(2.2.2)octan-3-one

HRID 1619321Notes

Reaction equation

HRID 1619321 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10]CC)=O)[CH2:4][CH2:3]1.C1(C)C=CC=CC=1>O>[CH:2]12[CH2:7][CH2:6][CH:5]([CH2:4][CH2:3]1)[C:8](=[O:10])[NH:1]2

Participants

4

Reactant 2

HCID 1140TolueneHCID 409963Ethyl 4-aminocyclohexanecarboxylate

Product 1

HCID 1378872-Azabicyclo(2.2.2)octan-3-oneYield 68.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of ethyl 4-aminocyclohexanecarboxylate (0.6 g, 3.49 mmol), toluene (1 mL) in oil bath (170° C.) was heated for 2-3 h to dryness. After cooling to rt, the reaction mixture was diluted with water and extracted with ethyl acetate (3×30 mL). The combined organic layers were dried over Na2SO4. After filtration and concentration, 300 mg of the desired product was obtained by column chromatography purification. MS (ESI): 126 (MH+).

Workup

  1. extractionextracted with ethyl acetate (3×30 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-db8b422812164847b82dc3fe39e45f40
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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