Piperazine → HCID 18549145, compound

HRID 1592722Notes

Reaction equation

HRID 1592722 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>O1CCOCC1>[NH2:11][S:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 4837Piperazine2×HCID 1936632-Fluorobenzenesulfonamide

Product 1

HCID 18549145HCID 18549145, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a 50 mL flask containing 2-flourobenzene sulfonamide (200 mg, 1.14 mmol, 1 eq.) and piperazine (245 mg, 2.84 mmol, 2.5 eq) was added 20 mL of dioxane. The solution was heated to 100° C. for about 4 hours. More piperazine (200 mg, 2.32 mmol, 2 eq.) was added and the solution was heated to 100° C. for another 72 hours. The solution was concentrated to an oil and dissolved in 30 mL of 0.1 M pH 7.0 phosphate buffer. The aqueous solution was extracted with CH2Cl2 (3×30 mL). The combined organic extracts were dried over Na2SO4 and concentrated to yield about 275 mg (1.14 mmol, 100%) of the title compound. LRMS (ESI+): 242.1 (M+H).

Workup

  1. temperaturethe solution was heated to 100° C. for another 72 hours
  2. concentrationThe solution was concentrated to an oil
  3. dissolutiondissolved in 30 mL of 0.1 M pH 7.0 phosphate buffer
  4. extractionThe aqueous solution was extracted with CH2Cl2 (3×30 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c6635f7be9364a228c7cd1679de03ec1
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Reaction notes

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