Piperidine → Piperidine-1-sulfonyl chloride

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

Reactant 2

HCID 8082Piperidine

HCID 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

custompartitioned between dichloromethane and water (50 mL)
washThe organic layer was washed with aqueous 1N HCl, brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
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
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902203B2

Reaction notes

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