Sodium Carbonate → Methyl 4-(2-methoxybenzyl)-1-piperazinecarbodithioate

HRID 1757553Notes

Reaction equation

HRID 1757553 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5]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:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][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 814952-(Chloromethyl)anisoleHCID 21278808Methyl piperazine-1-carbodithioate

Product 1

HCID 19388435Methyl 4-(2-methoxybenzyl)-1-piperazinecarbodithioateYield 44.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a nitrogen atmosphere, 2.28 g (14.5 mmol.) of 2-methoxybenzyl chloride, 2.69 g (14.5 mmol., purity 94.8%) of methyl 1-piperazinecarbodithioate, 1.53 g (14.5 mmol.) of anhydrous sodium carbonate and 15 ml of ethanol were mixed and refluxed under heating for 18 hours. Insolubles were removed by filtration, and the solvent of the filtrate was distilled off under reduced pressure. To the residue were added 15 ml of dichloromethaneand 15 ml of water. The organic solvent portion was taken out, washed with 17 ml of 1-N hydrochloric acid and 20 ml of 1-N aqueous sodium hydroxide solution, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by column chromatography to give 1.92 g of methyl 4-(2-methoxybenzyl)-1-piperazinecarbodithioate, yield 44.7%.

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 18 hours
  3. customInsolubles were removed by filtration
  4. distillationthe solvent of the filtrate was distilled off under reduced pressure
  5. additionTo the residue were added 15 ml of dichloromethaneand 15 ml of water
  6. washwashed with 17 ml of 1-N hydrochloric acid and 20 ml of 1-N aqueous sodium hydroxide solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-404b577fb82b4967b9ab4b88174469fb
Source dataset
uspto-grants-1995_08
Patent number
US05446146

Reaction notes

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