Piperidine → Piperidine-1-sulfonyl chloride

HRID 601413Notes

Reaction equation

HRID 601413 reaction equation
[S:1]([Cl:5])(Cl)(=[O:3])=[O:2].[NH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1>>[N:6]1([S:1]([Cl:5])(=[O:3])=[O:2])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

3

Reactant 2

HCID 8082PiperidineHCID 24648Sulfuryl chloride

Product 1

HCID 11298344Piperidine-1-sulfonyl chlorideYield 36.3%

Conditions

Temperature
0 °C

Procedure

A solution of sulfuryl chloride (1N in dichloromethane, 75 mL, 75 mmol) at −20° C. was treated dropwise with piperidine (12.6 g, 150 mmol), stirred at 0° C. for 2 hours, and partitioned between dichloromethane and water (50 mL). The organic layer was washed with aqueous 1N HCl, brine and dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was distilled under reduced pressure (1 mm Hg) at 105° C. to give the title compound (5 grams).

Workup

  1. custompartitioned between dichloromethane and water (50 mL)
  2. washThe organic layer was washed with aqueous 1N HCl, brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. distillationThe residue was distilled under reduced pressure (1 mm Hg) at 105° C.

Sources & evidence

ORD record
ord-42a00bc52f6140398ccdc6b6f995e306
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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