Methanol → Carbonic acid 1-(4-ethyl-phenyl)-2-[4-(4-fluoro-benzoyl)-piperidin-1-yl]-ethyl ester methyl ester

HRID 1835289Notes

Reaction equation

HRID 1835289 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]([C:18]1[CH:23]=[CH:22][C:21]([CH:24]2[CH2:26][O:25]2)=[CH:20][CH:19]=1)[CH3:17].[C:27](N1C=CN=C1)(N1C=CN=C1)=[O:28].[CH3:39][OH:40]>C(O)(C)C.O>[CH3:39][O:40][C:27](=[O:28])[O:25][CH:24]([C:21]1[CH:20]=[CH:19][C:18]([CH2:16][CH3:17])=[CH:23][CH:22]=1)[CH2:26][N:11]1[CH2:12][CH2:13][CH:8]([C:6](=[O:7])[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:15][CH:14]=2)[CH2:9][CH2:10]1

Participants

7

Reactant 4

HCID 887MethanolHCID 682631,1'-CarbonyldiimidazoleHCID 27244404-(4-Fluorobenzoyl)piperidineHCID 103745952-(4-Ethylphenyl)-oxirane

Product 1

HCID 11742469Carbonic acid 1-(4-ethyl-phenyl)-2-[4-(4-fluoro-benzoyl)-piperidin-1-yl]-ethyl ester methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of 4-(4-fluorobenzoyl)piperidine (5 mmol) and 2-(4-ethylphenyl)-oxirane (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 methanol (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 resulting carbonic acid 1-(4-ethyl-phenyl)-2-[4-(4-fluoro-benzoyl)-piperidin-1-yl]-ethyl ester methyl ester was obtained by column chromatography.

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

Sources & evidence

ORD record
ord-90d2bda0f6204f3aabef9bc568a8f257
Source dataset
uspto-grants-2004_08
Patent number
US06770659B2

Reaction notes

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