Hydrochloric Acid → HCID 18444273, compound

HRID 459870Notes

Reaction equation

HRID 459870 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[C:15]([C:17]([N:19]3[CH2:24][CH2:23][N:22]([C:25]4[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=4)[CH2:21][CH2:20]3)=[O:18])[CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[O:32]1[CH2:36][CH2:35]OC1=O.C(=O)([O-])[O-].[K+].[K+].Cl.C(=O)([O-])O.[Na+]>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[C:15]([C:17]([N:19]3[CH2:20][CH2:21][N:22]([C:25]4[CH:26]=[CH:27][C:28]([O:31][CH2:35][CH2:36][OH:32])=[CH:29][CH:30]=4)[CH2:23][CH2:24]3)=[O:18])[CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7303Ethylene carbonateHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 18444282HCID 18444282, compound

Product 1

HCID 18444273HCID 18444273, compoundYield 12.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To 297 mg of 4-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]-1-(4-hydroxyphenyl)piperazine were added 623 mg of [1,3]dioxolan-2-one and 147 mg of potassium carbonate, followed by 1.5 hours of stirring at 100° C. After the mixture was cooled to room temperature, water and then 1M hydrochloric acid were added to the reaction solution, which was then neutralized with a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with chloroform. The organic layer was washed with brine and then dried over anhydrous magnesium sulfate, and thereafter, the solvent was evaporated. The residue was purified by silica gel column chromatography (chloroform-methanol) and then recrystallization was carried out from ethyl acetate to obtain 41 mg of 2-(4-{4-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]piperazin-1-yl}phenoxy)ethanol as pale yellow crystals.

Workup

  1. temperatureAfter the mixture was cooled to room temperature
  2. extractionfollowed by extraction with chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified by silica gel column chromatography (chloroform-methanol)
  7. customrecrystallization

Sources & evidence

ORD record
ord-25e6f87c24794dfcbfc45201e58915d2
Source dataset
uspto-grants-2007_03
Patent number
US07196080B2

Reaction notes

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