Piperazine → Piperazine-1-carboximidamide

HRID 747094Notes

Reaction equation

HRID 747094 reaction equation
CC[N:3]([CH2:6]C)CC.[NH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.C1COCC1.C[N:20](C=O)C>C(#N)C.CCOCC.O1CCOCC1>[N:8]1([C:6]([NH2:3])=[NH:20])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1

Participants

8

Reactant 4

HCID 4837PiperazineHCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 8471Triethylamine

Product 1

HCID 2760424Piperazine-1-carboximidamide

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

Et3N (1-100 eq.) was added into a solution of 2-keto acyl chloride (1 eq.) and piperazine (1-5 eq.) in an aprotic solvent (such as THF, DMF, dioxane, ether, acetonitrile) and reaction was stirred at room temperature for 17 hours before quenched with saturated aqueous NaHCO3 solution. The aqueous layer was extracted with ethyl acetate. The organic phase combined and dried over anhydrous MgSO4. Concentration in vacuo provided a crude product, which was purified by tritaration, or recrystallization, or silica gel column chromatography, or Shimadzu automated preparative HPLC System.

Workup

  1. custombefore quenched with saturated aqueous NaHCO3 solution
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-58e09b577f5a4231b9d0df73312c6500
Source dataset
uspto-grants-2008_07
Patent number
US07396830B2

Reaction notes

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