Piperazine → N-diphenylphosphinoyl-piperazine

HRID 1070753Notes

Reaction equation

HRID 1070753 reaction equation
[Cl-].[C:2]1([P:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(=[O:10])[O-])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>CN(C=O)C>[C:11]1([P:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[O:10])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 22397669Diphenylphosphinate chloride

Product 1

HCID 22397667N-diphenylphosphinoyl-piperazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

20 g (84.5 mmol) diphenylphosphinate chloride dissolved in 30 ml DMF are added dropwise to a solution of 21.8 g (253 mmol) piperazine in DMF. After four hours, the solution is concentrated under vacuum, taken up in chloroform and extracted by shaking with 10% hydroxide solution. The organic phase is dried over sodium sulfate and solvent is removed under vacuum. The residue is chromatographically purified over silica gel with CHCl3/CH3OH/TEA (90/10/0 to 90/10/6): yield 12 g (49%).

Workup

  1. concentrationthe solution is concentrated under vacuum
  2. extractionextracted
  3. dry with materialThe organic phase is dried over sodium sulfate and solvent
  4. customis removed under vacuum
  5. customThe residue is chromatographically purified over silica gel with CHCl3/CH3OH/TEA (90/10/0 to 90/10/6)

Sources & evidence

ORD record
ord-daac661371474c20830d39a95aa25eb9
Source dataset
uspto-grants-2005_06
Patent number
US06903118B1

Reaction notes

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