Piperazine → HCID 43344301, compound

HRID 597829Notes

Reaction equation

HRID 597829 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[F:14][C:15]1[CH:16]=[CH:17][C:18]([CH3:25])=[C:19]([S:21](Cl)(=[O:23])=[O:22])[CH:20]=1>C(OCC)C.CCOC(C)=O.C([O-])(O)=O.[Na+]>[F:14][C:15]1[CH:16]=[CH:17][C:18]([CH3:25])=[C:19]([S:21]([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)(=[O:23])=[O:22])[CH:20]=1

Participants

7

Reactant 3

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

Product 1

HCID 43344301HCID 43344301, compoundYield 55.4%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of piperazine (28.4 g, 288 mmol) in triethylamine (42 mL, 300 mmol) and diethyl ether (500 mL) that was cooled to 0° C. was added dropwise a solution of 5-fluoro-2-methylbenzene sulfonylchloride (30 g, 144 mmol) dissolved in diethyl ether (50 mL). The resulting mixture was stirred at room temp for 2 h then diluted with EtOAc and saturated aqueous NaHCO3. The organic phase was washed with water, brine and dried (Na2SO4). Concentration gave the title compound as a white solid (20.6 g, 55% 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 organic phase was washed with water, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationConcentration

Sources & evidence

ORD record
ord-ace081e39022420bac7f02f7270dd445
Source dataset
uspto-grants-2011_03
Patent number
US07897593B2

Reaction notes

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