Water → HCID 53823074, compound

HRID 1816736Notes

Reaction equation

HRID 1816736 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8](F)=[CH:7][CH:6]=1)[CH3:2].[C:13]1([CH:19]2[CH2:24][CH2:23][N:22]([C:25]3[CH:30]=[CH:29][C:28]([N:31]4[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]4)=[CH:27][CH:26]=3)[CH2:21][CH2:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([N:34]2[CH2:33][CH2:32][N:31]([C:28]3[CH:29]=[CH:30][C:25]([N:22]4[CH2:21][CH2:20][CH:19]([C:13]5[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=5)[CH2:24][CH2:23]4)=[CH:26][CH:27]=3)[CH2:36][CH2:35]2)=[CH:7][CH:6]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 22494741HCID 22494741, compound

Product 1

HCID 53823074HCID 53823074, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-fluorobenzoic acid ethyl ester (1.25 g), 1-[4-(4-phenylpiperidin-1-yl)phenyl]piperazine (1.19 g) and potassium carbonate (1.53 g) in dimethylsulfoxide (18 ml) was stirred for 12 hours at 150° C. The reaction mixture was pulverized with water. The mixture was extracted with dichloromethane. The organic layer was separated, washed with brine, dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography over silica using dichloromethane/methyl alcohol (200:1) as the elution. The powder was recrystallized from toluene (60 ml). The crystal was collected by filtration, and dried under reduced pressure to give 4-[4-[4-(4-phenylpiperidin-1-yl)phenyl]piperazin-1-yl]benzoic acid ethyl ester (0.80 g).

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe magnesium sulfate was filtered off
  6. customthe filtrate was evaporated under reduced pressure
  7. customThe residue was purified by column chromatography over silica
  8. washas the elution
  9. customThe powder was recrystallized from toluene (60 ml)
  10. filtrationThe crystal was collected by filtration
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-251604ea6adb424bad3d0857a9f3d825
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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