Benzyl Chloride → 1-Benzyl-3-methylpiperazine

HRID 2399225Notes

Reaction equation

HRID 2399225 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][CH:10]1[CH2:15][NH:14][CH2:13][CH2:12][NH:11]1.C([O-])([O-])=O.[K+].[K+]>[Na+].[I-].C(C(C)=O)C>[CH2:1]([N:14]1[CH2:13][CH2:12][NH:11][CH:10]([CH3:9])[CH2:15]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 660572-Methylpiperazine

Product 1

HCID 27275201-Benzyl-3-methylpiperazineYield 28.9%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 6569Methyl Ethyl KetoneSolvent

Procedure

To 500 ml of ice cooled methyl ethyl ketone, 126.5 g (1 mol) of benzyl chloride, 100 g (1 mol) of 2-methylpiperazine, 138 g (1 mol) of anhydrous K2CO3 and 2 g of NaI are added. The mixture is stirred at the reflux temperature for 2 hours, then cooled to room temperature; K2CO3 is filtered off and the solvent evaporated. The residue is dissolved in diluted NaOH, extracted with some ethyl ether, washed with water, dried over Na2SO4 and the solvent is evaporated off to provide 55 g of 1-benzyl-3-methylpiperazine. B.p. 140°-150° C./20-25 mmHg.

Workup

  1. additionare added
  2. filtrationK2CO3 is filtered off
  3. customthe solvent evaporated
  4. dissolutionThe residue is dissolved in diluted NaOH
  5. extractionextracted with some ethyl ether
  6. washwashed with water
  7. dry with materialdried over Na2SO4
  8. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-9045c3002eb94e69b800e09107f9adc5
Source dataset
uspto-grants-1995_09
Patent number
US05447931

Reaction notes

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