Piperidine → 1-[(5-Bromo-2-thienyl)sulfonyl]piperidine

HRID 2267327Notes

Reaction equation

HRID 2267327 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:7][C:8]1[S:12][C:11]([S:13](Cl)(=[O:15])=[O:14])=[CH:10][CH:9]=1.C(N(CC)CC)C>O1CCCC1.[Cl-].[Na+].O>[Br:7][C:8]1[S:12][C:11]([S:13]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:15])=[O:14])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 8471TriethylamineHCID 27339245-Bromothiophene-2-sulfonyl chloride

Product 1

HCID 5586101-[(5-Bromo-2-thienyl)sulfonyl]piperidine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Piperidine (0.72 g, 8.41 mmol) was added to a solution of 5-bromothiophene-2-sulfonyl chloride (2 g, 7.65 mmol) in tetrahydrofuran (100 mL) at 0° C. followed by triethylamine (0.93 g, 9.18 mmol) added slowly. The resulting mixture was stirred at rt overnight and 100 mL of brine was added. The mixture was extracted with ethyl acetate (3×100 mL). The combined organic layer was washed with brine (100 mL), dried over anhydrous sodium sulfate and filtered. Removal of the solvent gave the title compound as a slightly yellow solid (quantitative yield).

Workup

  1. additionadded slowly
  2. extractionThe mixture was extracted with ethyl acetate (3×100 mL)
  3. washThe combined organic layer was washed with brine (100 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-5a9436edb70345df8fd366d6aa68a29a
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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