Benzenesulfonyl chloride → HCID 44237012, compound

HRID 1868005Notes

Reaction equation

HRID 1868005 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[C:4]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[N:5][CH:6]=[CH:7][CH:8]=1.[C:17]1([S:23](Cl)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl.C(=O)(O)[O-].[Na+].O>[C:17]1([S:23]([N:12]2[CH2:11][CH2:10][N:9]([C:4]3[C:3]([C:2]([F:1])([F:15])[F:16])=[CH:8][CH:7]=[CH:6][N:5]=3)[CH2:14][CH2:13]2)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 27777861-[3-(Trifluoromethyl)pyridin-2-yl]piperazine

Product 1

HCID 44237012HCID 44237012, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 1-[3-(trifluoromethyl)-2-pyridyl]piperazine (60 mg, 0.26 mmol), and Benzene sulfonyl chloride (0.043 mL, 0.31 mmol) in DCM (4 mL) and saturated sodium bicarbonate (2 mL) was stirred at room temperature for 12 hours. The mixture was diluted with DCM (5 mL) and water (5 mL). The organic layer was collected and washed two times with water, dried with magnesium sulfate, and concentrated. The product was purified using column chromatography (20% Ethyl Acetate in Hexanes) to produce 1-(phenylsulfonyl)-4-[3-(trifluoromethyl)pyridin-2-yl]piperazine (81.1 mg, 84%).

Workup

  1. customThe organic layer was collected
  2. washwashed two times with water
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated
  5. customThe product was purified

Sources & evidence

ORD record
ord-f38cb292be7c4cadb545c84d2b55bafb
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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