Pyrrolidine → 1-Methyl-4-(pyrrolidinocarbonyl)piperazine

HRID 904813Notes

Reaction equation

HRID 904813 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8](Cl)=[O:9])[CH2:4][CH2:3]1.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1>C1(C)C=CC=CC=1>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:9])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 30169354-Methyl-1-piperazinecarbonyl chloride

Product 1

HCID 130230081-Methyl-4-(pyrrolidinocarbonyl)piperazine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

In 50 ml of toluene was dissolved 8.1 g (0.05 mole) of 1-methyl-4-chlorocarbonylpiperazine at room temperature and a solution of 10.7 g (0.15 mole) of pyrrolidine in 50 ml of toluene was dropped to the above solution at 0° C. over a period of 30 minutes. The mixture was refluxed for 1 hour to complete the reaction. The reaction mixture was cooled, and the precipitated yellow crystal (pyrrolidine hydrochloride) was removed by filtration. The filtrate was dried with anhydrous sodium sulfate and toluene as the solvent was removed by distillation under reduced pressure to obtain crude 1-methyl-4-(pyrrolidinocarbonyl)piperazine as the distillation residue. The crude product was purified by distillation under reduced pressure to obtain 6.6 g of a pure product having a boiling point of 109.5 to 110.0° C. at 0.5-0.6 mm Hg obs. The yield was 66.9%. The elementary analysis values are as follows:

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. customthe reaction
  3. temperatureThe reaction mixture was cooled
  4. customthe precipitated yellow crystal (pyrrolidine hydrochloride) was removed by filtration
  5. dry with materialThe filtrate was dried with anhydrous sodium sulfate and toluene as the solvent
  6. customwas removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-35b3893e10a04154ae3e1179514654a5
Source dataset
uspto-grants-1983_12
Patent number
US04420481

Reaction notes

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