Tetrahydrofuran → HCID 18538548, compound

HRID 412903Notes

Reaction equation

HRID 412903 reaction equation
Cl[S:2](Cl)(=[O:4])=[O:3].[OH2:6].[NH3:7].[CH2:8]([N:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[CH3:9].[CH2:15]1[CH2:19]O[CH2:17][CH2:16]1>>[C:8]([N:10]1[CH2:13][CH2:14][CH:17]([CH2:16][C:15]2[CH:19]=[CH:17][C:16]([S:2]([NH2:7])(=[O:4])=[O:3])=[CH:15][CH:19]=2)[CH2:12][CH2:11]1)(=[O:6])[CH3:9]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 24648Sulfuryl chlorideHCID 12896473Azane;hydrate

Product 1

HCID 18538548HCID 18538548, compoundYield 78%

Procedure

To chlorosulfonic acid (3.1 mL) was added dropwise a solution of 1-acetyl-4-benzylpiperidine (2.0 g) in chloroform (5 mL) under ice cooling, and the mixture was stirred at, the same temperature for 1 hour and at room temperature for 30 minutes. The reaction mixture was poured into ice-water, and the mixture was extracted with chloroform. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to give chlorosulfone derivatives (1.87 g). A solution of the above chlorosulfone derivatives (1.04 g), 10% ammonia water (12 mL) and triethylamine (0.92 mL) in THF (20 mL) was heated for 1.5 hour under ref lux. The organic solvent was distilled off, and the residue was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The concentrate was subjected to silica gel column chromatography (ethyl acetate/methanol=8/1), and the desired fraction was concentrated under reduced pressure to give the titled compound (0.755 g, 2.55 mmol, Yield 78%) as a colorless oily substance.

Workup

  1. temperaturewas heated for 1.5 hour under ref lux
  2. distillationThe organic solvent was distilled off
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. concentrationthe desired fraction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-68aee352ef7343e3b89ce94da7edbc64
Source dataset
uspto-grants-2003_05
Patent number
US06562978B1

Reaction notes

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