1-Methylpiperazine → HCID 57066993, compound

HRID 2295034Notes

Reaction equation

HRID 2295034 reaction equation
[C:1]1([CH:7]=[N:8][N:9]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17]I)[C:10]2=[O:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>CN(C)C=O>[C:1]1([CH:7]=[N:8][N:9]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][N:24]3[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]3)[C:10]2=[O:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 57037835HCID 57037835, compound

Product 1

HCID 57066993HCID 57066993, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 1-phenylmethyleneamino-3-(4-iodobutyl)-2-imidazolidinone (10.0 g, 0.0269 mole), dimethylformamide (150 ml) and 1-methylpiperazine (6.0 ml, 3.4 g, 0.0539 mole) is heated to reflux. Reflux is maintained for 2.5 hours. The solution is concentrated under reduced pressure to a semi-solid residue. This residue is dissolved in CHCl3 (300 ml), then washed with saturated NaHC3 solution. (3×400 ml), H2O (2×100 ml) and dried over MgSO4. The filtered solution is concentrated under reduced pressure to an oily residue. This residue is triturated in hexane (300 ml) by stirring. The solid is collected and air-dried to give 8.0 g (0.0233 mole) of 1-phenylmethyleneamino-3-[4-(4-methyl-1-piperazinyl)butyl]-2-imidazolidinone.

Workup

  1. temperatureReflux
  2. temperatureis maintained for 2.5 hours
  3. concentrationThe solution is concentrated under reduced pressure to a semi-solid residue
  4. dissolutionThis residue is dissolved in CHCl3 (300 ml)
  5. washwashed with saturated NaHC3 solution
  6. dry with material(3×400 ml), H2O (2×100 ml) and dried over MgSO4
  7. concentrationThe filtered solution is concentrated under reduced pressure to an oily residue
  8. customThis residue is triturated in hexane (300 ml)
  9. customThe solid is collected
  10. customair-dried

Sources & evidence

ORD record
ord-044215e174ec49689f46fa81af76b11e
Source dataset
uspto-grants-1997_11
Patent number
US05691369

Reaction notes

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