Azepane → HCID 22228387, compound

HRID 656439Notes

Reaction equation

HRID 656439 reaction equation
F[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[NH:12]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>N1C=CC=CC=1>[N:12]1([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[C:7](=[O:11])[CH2:6][CH2:5]3)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 8119AzepaneHCID 1365375-Fluoro-1-indanone

Product 1

HCID 22228387HCID 22228387, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Fluoroindan-1-one (5 g, 33.3 mmol) and azepane (9.92 g, 100 mmol) were dissolved in pyridine (20 ml) and heated at reflux for 3 hours, stirred at ambient temperature for 16 hours, and then heated at reflux for an additional 6 hours. The solvent was removed under vacuum and the residue partitioned between methylene chloride and water. The organic layer was washed with 1N aqueous sodium hydroxide, dried with magnesium sulfate, filtered, and the filtrate was concentrated under vacuum. The residue was filtered through a pad of silica gel with 1:1 ethyl acetate:hexanes, and the solvent evaporated under vacuum to provide the title compound which was used without further purification. 1H NMR (CDCl3) δ 1.56 (m, 4H), 1.81 (m, 4H), 2.62 (m, 2H), 3.02 (m, 2H), 3.55 (t, 4H), 6.59 (d, 1H), 6.68 (dd, 1H), 7.61 (d, 1H); MS (DCI) 230 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. temperatureheated
  4. temperatureat reflux for an additional 6 hours
  5. customThe solvent was removed under vacuum
  6. customthe residue partitioned between methylene chloride and water
  7. washThe organic layer was washed with 1N aqueous sodium hydroxide
  8. dry with materialdried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationthe filtrate was concentrated under vacuum
  11. filtrationThe residue was filtered through a pad of silica gel with 1:1 ethyl acetate
  12. customhexanes, and the solvent evaporated under vacuum

Sources & evidence

ORD record
ord-52d5320a2a264bddbf01c2759643b961
Source dataset
uspto-grants-2011_12
Patent number
US08071762B2

Reaction notes

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