Styrene Oxide → 666859-31-0

HRID 1835286Notes

Reaction equation

HRID 1835286 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[CH2:16]1[O:24][CH:17]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[C:25]([N:32]1C=CN=C1)(N1C=CN=C1)=[O:26].[OH-].[NH4+]>C(O)(C)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:16][CH:17]([O:24][C:25](=[O:26])[NH2:32])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:10][CH2:9]2)=[O:7])=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 7276Styrene OxideHCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 27244404-(4-Fluorobenzoyl)piperidine

Product 1

HCID 10339127666859-31-0

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of 4-(4-fluorobenzoyl)piperidine (5 mmol) and styrene oxide(5 mmol) was refluxed in 30 ml of isopropanol for 4 h. This solution was then concentrated on a rotary evaporator and diluted with ethyl acetate. This mixture was then washed with brine, the resulting organic layer was dried and concentrated in vacuo. The crude product was dissolved in THF(50 ml) and was added with 1,1′-carbonyl diimidazole (2 mmol) at 0° C. The reaction mixture was stirred at room temperature for 4 h, followed by the addition of excess ammonium hydroxide (10 ml) at 0° C. After 5 h stirring at room temperature, water was added to terminate the reaction. The organic layer was extracted 3 times with dichloromethane, dried and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate:hexane=1:2). The resulting carbamic acid 2-[4-(4-fluoro-benzoyl)-piperidin-1-yl]-1-phenyl-ethyl ester was dissolved in THF and the solution was treated with a solution of HCl in ethyl ether. The resulting precipitate was filtered to give carbamic acid 2-[4-(4-fluoro-benzoyl)-piperidin-1-yl]-1-phenyl-ethyl ester; hydrochloride.

Workup

  1. concentrationThis solution was then concentrated on a rotary evaporator
  2. additiondiluted with ethyl acetate
  3. washThis mixture was then washed with brine
  4. customthe resulting organic layer was dried
  5. concentrationconcentrated in vacuo
  6. dissolutionThe crude product was dissolved in THF(50 ml)
  7. stirringAfter 5 h stirring at room temperature
  8. customto terminate
  9. customthe reaction
  10. extractionThe organic layer was extracted 3 times with dichloromethane
  11. customdried
  12. concentrationconcentrated in vacuo
  13. customThe residue was purified by column chromatography (ethyl acetate:hexane=1:2)
  14. dissolutionThe resulting carbamic acid 2-[4-(4-fluoro-benzoyl)-piperidin-1-yl]-1-phenyl-ethyl ester was dissolved in THF
  15. additionthe solution was treated with a solution of HCl in ethyl ether
  16. filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record
ord-3924d559008340ea8bdd9050f4001c3a
Source dataset
uspto-grants-2004_08
Patent number
US06770659B2

Reaction notes

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