Aniline → HCID 68555117, compound

HRID 2036088Notes

Reaction equation

HRID 2036088 reaction equation
[CH2:1]([N:8]1[CH2:14][CH2:13][C:10]2([O:12][CH2:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl([O-])(=O)(=O)=O.[Li+]>C(#N)C>[NH:15]([CH2:11][C:10]1([OH:12])[CH2:13][CH2:14][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 111948055-Benzyl-1-oxa-5-azaspiro[2.4]heptaneHCID 23665649Lithium perchlorate

Product 1

HCID 68555117HCID 68555117, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

5-Benzyl-1-oxa-5-azaspiro[2.4]heptane (946 mg) was dissolved in acetonitrile (30 mL), and aniline (0.55 mL) and lithium perchlorate (640 mg) were added. After stirring at 80° C. overnight, the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate, and the solution was washed twice with aqueous sodium hydrogen carbonate solution. The organic layer was dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography using basic silica gel (20% ethyl acetate/hexane to 60% ethyl acetate/hexane) to give the object product (768 mg, 54%).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washthe solution was washed twice with aqueous sodium hydrogen carbonate solution
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f9e6cc9dcb464fd3a50a2f623691cb67
Source dataset
uspto-grants-2013_11
Patent number
US08575167B2

Reaction notes

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