Piperidine → 1-(thiophen-2-ylsulfonyl)piperidine

HRID 2267441Notes

Reaction equation

HRID 2267441 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6](Cl)(=[O:8])=[O:7].[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>ClCCl>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)(=[O:8])=[O:7]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 855182-Thiophenesulfonyl chloride

Product 1

HCID 7658231-(thiophen-2-ylsulfonyl)piperidineYield 95.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Thiophene-2-sulfonyl chloride (10 g, 54 mmol) was dissolved in dichloromethane (15 mL) and added dropwise to a round-bottom flask containing a solution of piperidine (10.6 mL, 108 mmol) and diisopropylethyilamine (18.8 mL, 108 mmol) in dichloromethane at 0° C. The reaction was stirred at 0° C. for 15 min and then allowed to warm up to room temperature. After 2 h, the reaction was washed successively with a saturated solution of sodium bicarbonate, water, 1 N HCl and a saturated solution of sodium chloride. The organic layer was dried with sodium sulfate, concentrated and placed on a vacuum line to give an off-white solid (11.98 g). MS (M+H)+ 232.

Workup

  1. additionadded dropwise to a round-bottom flask
  2. temperatureto warm up to room temperature
  3. waitAfter 2 h
  4. washthe reaction was washed successively with a saturated solution of sodium bicarbonate, water, 1 N HCl
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-56d607fbfd7f4dbabe5a7773c05be5fa
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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