Water → HCID 67402255, compound

HRID 1186432Notes

Reaction equation

HRID 1186432 reaction equation
[F:1][C:2]1([CH:8]([O:13][Si:14]([CH2:19][CH3:20])([CH2:17][CH3:18])[CH2:15][CH3:16])[C:9]([F:12])([F:11])[F:10])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30].O>ClCCl>[F:1][C:2]1([CH:8]([O:13][Si:14]([CH2:17][CH3:18])([CH2:19][CH3:20])[CH2:15][CH3:16])[C:9]([F:11])([F:12])[F:10])[CH2:3][CH2:4][N:5]([S:29]([CH3:28])(=[O:31])=[O:30])[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67401528HCID 67401528, compound

Product 1

HCID 67402255HCID 67402255, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Fluoro-4-[2,2,2-trifluoro-1-(triethylsiloxy)ethyl]-piperidine (300 mg, 0.951 mmol) was dissolved in dichloromethane (6 mL). To this, triethylamine (0.199 mL, 1.43 mmol) and methanesulfonyl chloride (0.140 mL, 1.43 mmol) were added and the mixture was stirred at room temperature for 30 minutes. The reaction was stopped by addition of water to the reaction mixture, and extraction with dichloromethane was performed, followed by 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=7/3) to give 4-fluoro-1-methanesulfonyl-4-[2,2,2-trifluoro-1-(triethyl-siloxy)ethyl]piperidine (309 mg, yield: 83%).

Workup

  1. dry with materialby drying over anhydrous sodium sulfate
  2. customThe solvent was evaporated off under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3)

Sources & evidence

ORD record
ord-71f942cfe3e44520b4991451480df51b
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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