Sodium Carbonate → Methyl 4-(3-methoxybenzyl)-1-piperazinecarbodithioate

HRID 1757563Notes

Reaction equation

HRID 1757563 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6]Cl.[N:11]1([C:17]([S:19][CH3:20])=[S:18])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][N:14]1[CH2:15][CH2:16][N:11]([C:17]([S:19][CH3:20])=[S:18])[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 699943-Methoxybenzyl chlorideHCID 21278808Methyl piperazine-1-carbodithioate

Product 1

HCID 19388481Methyl 4-(3-methoxybenzyl)-1-piperazinecarbodithioateYield 82.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a nitrogen atmosphere, 1.57 g (10.0 mmol.) of 3-methoxybenzyl chloride, 2.00 g (10.0 mmol., purity 88.1% of methyl 1-piperazinecarbodithioate, 1.06 g (10.0 mmol.) of anhydrous sodium carbonate and 20 ml of ethanol. The mixtrue was refluxed under heating for 5 hours. The solvent was distilled off under reduced pressure. The residue was mixed with 15 ml of dichloromethane and 10 ml of water. The mixture was allowed to give separated layers. The organic solvent portion was washed with water and a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and placed under reduced pressure to distill off the solvent. Theresidue was purified over a silica gel column to give 2.46 g of methyl 4-(3-methoxybenzyl)-1-piperazinecarbodithioate as a colorless crystalline product, yield 82.8%.

Workup

  1. temperatureThe mixtrue was refluxed
  2. temperatureunder heating for 5 hours
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionThe residue was mixed with 15 ml of dichloromethane and 10 ml of water
  5. customto give
  6. customseparated layers
  7. washThe organic solvent portion was washed with water
  8. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  9. distillationto distill off the solvent
  10. customTheresidue was purified over a silica gel column

Sources & evidence

ORD record
ord-ef57e3f420914cf7aec4f0854115f611
Source dataset
uspto-grants-1995_08
Patent number
US05446146

Reaction notes

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