Sodium Carbonate → Methyl 4-(3,4-dimethoxybenzyl)-1-piperazinecarbodithioate

HRID 1460180Notes

Reaction equation

HRID 1460180 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:6]Cl.[N:13]1([C:19]([S:21][CH3:22])=[S:20])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]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][C:10]=1[O:11][CH3:12])[CH2:6][N:16]1[CH2:17][CH2:18][N:13]([C:19]([S:21][CH3:22])=[S:20])[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 81740Veratryl chlorideHCID 21278808Methyl piperazine-1-carbodithioate

Product 1

HCID 19388443Methyl 4-(3,4-dimethoxybenzyl)-1-piperazinecarbodithioateYield 14.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a nitrogen atmosphere, 5.615 g (30.08 mmol.) of 3,4-dimethoxybenzyl chloride, 5.57 g (30.08 mmol., purity 95%) of methyl 1-piperazinecarbodithioate, 3.19 g (30.08 mmol.) of anhydrous sodium carbonate and 50 ml of ethanol were mixed and refluxed under heating for 5.5 hours. The solvent was distilled off under reduced pressure. To the residue were added 20 ml of dichloromethane and 20 ml of water. The organic solvent portion was taken out and washed with 30 ml of 1-N hydrochloric acid. To the organic portion was added 1-N aqueous sodium hydroxide solution. The organic solvent portion was again taken out and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. To the residue was added 20 ml of ethanol. Precipitated crystals were collected by filtration and washed with ethanol to give 1.465 g of methyl 4-(3,4-dimethoxybenzyl)-1-piperazinecarbodithioate, yield 14.9%.

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 5.5 hours
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionTo the residue were added 20 ml of dichloromethane and 20 ml of water
  5. washwashed with 30 ml of 1-N hydrochloric acid
  6. additionTo the organic portion was added 1-N aqueous sodium hydroxide solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. additionTo the residue was added 20 ml of ethanol
  10. customPrecipitated crystals
  11. filtrationwere collected by filtration
  12. washwashed with ethanol

Sources & evidence

ORD record
ord-d3d573bda2ed4f62994fad9562a3d979
Source dataset
uspto-grants-1991_12
Patent number
US05070089

Reaction notes

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