Hydrochloric Acid → HCID 58181350, compound

HRID 1465488Notes

Reaction equation

HRID 1465488 reaction equation
C([O:4][CH2:5][CH2:6][C:7]1[S:8][C:9]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][N:23]([C:26](=[O:28])[CH3:27])[CH2:22][CH2:21]3)=[CH:16][N:15]=2)=[CH:10][CH:11]=1)(=O)C.[OH-].[Na+].O.Cl>O1CCOCC1>[C:26]([N:23]1[CH2:24][CH2:25][N:20]([C:17]2[CH:18]=[CH:19][C:14]([CH2:13][CH2:12][C:9]3[S:8][C:7]([CH2:6][CH2:5][OH:4])=[CH:11][CH:10]=3)=[N:15][CH:16]=2)[CH2:21][CH2:22]1)(=[O:28])[CH3:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 58181263HCID 58181263, compound

Product 1

HCID 58181350HCID 58181350, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-(5-{2-[5-(4-acetylpiperazin-1-yl)pyridin-2-yl]ethyl}thiophen-2-yl)ethyl acetate (719.0 mg, 1.791 mmol) in dioxane (6.3 ml) were added 1M aqueous sodium hydroxide solution (6.27 ml, 6.27 mmol) and water (6.3 ml) at 0° C. After stirring at room temperature for 1 hr, the mixture was cooled to 0° C., and 1M hydrochloric acid (8.0 ml, 8.0 mmol) was added. The mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted 3 times with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:acetone=7:3→5:5) to give 2-(5-{2-[5-(4-acetylpiperazin-1-yl)pyridin-2-yl]ethyl}thiophen-2-yl)ethanol (608.7 mg, yield 94.5%) as a white solid.

Workup

  1. temperaturethe mixture was cooled to 0° C.
  2. concentrationThe mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution
  3. additionwas added to the residue
  4. extractionthe mixture was extracted 3 times with ethyl acetate
  5. washThe combined organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate:acetone=7:3→5:5)

Sources & evidence

ORD record
ord-d89335a0338d408c9028831f98e27306
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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