Piperazine → 1,4-Di-[(N,N'-di-p-tolyl)amidino]piperizine

HRID 1813886Notes

Reaction equation

HRID 1813886 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:7]1([CH3:23])[CH:12]=[CH:11][C:10]([N:13]=[C:14]=[N:15][C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)=[CH:9][CH:8]=1>CN(C=O)C>[C:7]1([CH3:23])[CH:12]=[CH:11][C:10]([NH:13][C:14]([N:1]2[CH2:6][CH2:5][N:4]([C:14](=[N:13][C:10]3[CH:11]=[CH:12][C:7]([CH3:23])=[CH:8][CH:9]=3)[NH:15][C:16]3[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=3)[CH2:3][CH2:2]2)=[N:15][C:16]2[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 69763Di-p-tolylcarbodiimide

Product 1

HCID 98284351,4-Di-[(N,N'-di-p-tolyl)amidino]piperizineYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.5 mmol of piperazine was dissolved in 10 ml of DMF and 1.05 mmol of 1,3 di-p-tolylcarbodiimide was added. After 0.5 h. of stirring at room temperature, a small precipitation was filtered off and washed twice with 1 ml of DMF. The filtrates were collected and kept at room temperature overnight. To the DMF solution, 50 ml of water was added. The precipitated solid was filtered and washed with water. The solid was dissolved in ethyl acetate (20 ml) and 0.2 ml of conc. HCl conc. was added. The product began to precipitate within 15 min. After 1 hour, the precipitate was filtered and washed with ethyl ether. Yield=76%.

Workup

  1. customa small precipitation
  2. filtrationwas filtered off
  3. washwashed twice with 1 ml of DMF
  4. customThe filtrates were collected
  5. waitkept at room temperature overnight
  6. additionTo the DMF solution, 50 ml of water was added
  7. filtrationThe precipitated solid was filtered
  8. washwashed with water
  9. dissolutionThe solid was dissolved in ethyl acetate (20 ml)
  10. addition0.2 ml of conc. HCl conc. was added
  11. customto precipitate within 15 min
  12. waitAfter 1 hour
  13. filtrationthe precipitate was filtered
  14. washwashed with ethyl ether

Sources & evidence

ORD record
ord-043855a5a4ea4824a411c7c077dd6982
Source dataset
uspto-grants-2005_04
Patent number
US06875759B1

Reaction notes

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