Hydrochloric Acid → HCID 67402269, compound

HRID 1186421Notes

Reaction equation

HRID 1186421 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH:8]([CH:11]([O:16][Si](CC)(CC)CC)[C:12]([F:15])([F:14])[F:13])[CH2:7][CH2:6]1)(=[O:4])=[O:3].Cl.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>O1CCCC1>[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH:8]([CH:11]([OH:16])[C:12]([F:15])([F:14])[F:13])[CH2:7][CH2:6]1)(=[O:3])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 67401456HCID 67401456, compound

Product 1

HCID 67402269HCID 67402269, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Methanesulfonyl-4-[2,2,2-trifluoro-1-(triethyl-siloxy)ethyl]piperidine (300 mg, 0.999 mmol) was dissolved in tetrahydrofuran (2.4 mL). To this, a 1 mol/L aqueous hydrogen chloride solution (2.4 mL) was added and the mixture was stirred at room temperature for 2 hours. The reaction was stopped by addition of a saturated aqueous sodium bicarbonate solution to the reaction mixture, and extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give Compound EAG (198 mg, yield: 95%).

Workup

  1. washby washing with brine
  2. dry with materialdrying over anhydrous sodium sulfate
  3. customThe solvent was evaporated off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)
  5. customto give Compound EAG (198 mg, yield: 95%)

Sources & evidence

ORD record
ord-3f1655af745943b2beb8561f426e13c3
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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