Piperazine → HCID 43344301, compound

HRID 600209Notes

Reaction equation

HRID 600209 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([S:8](Cl)(=[O:10])=[O:9])[CH:7]=1.[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(N(CC)CC)C>C(OCC)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([S:8]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)(=[O:10])=[O:9])[CH:7]=1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 8471TriethylamineHCID 1362865-Fluoro-2-methylbenzenesulphonyl chloride

Product 1

HCID 43344301HCID 43344301, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

5-Fluoro-2-methylbenzenesulfonyl chloride (35.1 g, 168.5 mmol) in diethyl ether (50 mL) was added drop-wise to a suspension of piperazine (28.8 g, 337.0 mmol) in diethyl ether (500 mL) and triethylamine (47 mL, 337.0 mmol). The white suspension was stirred at room temp for 1.5 h. The mixture was washed with saturated aqueous sodium carbonate. The organic phase was washed with water and brine and dried (Na2SO4). Concentration gave a white solid that was triturated with diethyl ether to give the title compound as a white solid (30.95 g, 36% yield). 1H NMR (300 MHz, CDCl3) δ: 7.57 (1H, dd, J=8.6, 2.7 Hz), 7.25 (1H, dd, J=8.4, 5.1 Hz), 7.12 (1H, td, J=8.1, 2.8 Hz), 3.13-3.10 (4H, m), 2.98-2.85 (4H, m), 2.55 (3H, s), 1.69 (1H, bs). LCMS (M+H) calcd for C11H16FN2O2S: 259.09; found: 259.18.

Workup

  1. washThe mixture was washed with saturated aqueous sodium carbonate
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationConcentration
  5. customgave a white solid
  6. customthat was triturated with diethyl ether

Sources & evidence

ORD record
ord-7652baa5bc9a46c2a655d68797bc641f
Source dataset
uspto-grants-2011_03
Patent number
US07902182B2

Reaction notes

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