4-Methoxybenzyl alcohol → Methyl 4-(4-methoxybenzyl)-1-piperazinecarbodithioate

HRID 1757562Notes

Reaction equation

HRID 1757562 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]O)=[CH:5][CH:4]=1.S(Cl)(Cl)=O.[N:15]1([C:21]([S:23][CH3:24])=[S:22])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.C(O)C>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][N:18]2[CH2:19][CH2:20][N:15]([C:21]([S:23][CH3:24])=[S:22])[CH2:16][CH2:17]2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 77384-Methoxybenzyl alcoholHCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 21278808Methyl piperazine-1-carbodithioate

Product 1

HCID 19388511Methyl 4-(4-methoxybenzyl)-1-piperazinecarbodithioateYield 34%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

In a nitrogen atmosphere, 2.00 g (14.5 mmol.) of 4-methoxybenzyl alcohol was dissolved in 10 ml of dichloromethane. Under chilling with ice, to thesolution was dropwise added a solution of 1.05 ml (14.5 mmol.) of thionyl chloride in 2 ml of dichloromethane. The mixture was then stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure. The residue was mixed with 2.90 g (14.5 mmol., purity 88.1%) of methyl 1-piperazinecarbodithioate, 1.54 g (14.5 mmol.) of anhydrous sodiumcarbonate and 25 ml of ethanol. The mixtrue was refluxed under heating for 14.5 hours. The solvent was distilled off under reduced pressure. The residue was mixed with 10 ml of dichloromethane and 10 ml of water. The mixture was allowed to give separated layers, and filtered to remove insolubles. 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 1.46 g of methyl 4-(4-methoxybenzyl)-1-piperazinecarbodithioate as a pale yellow oil, yield33.9%.

Workup

  1. temperatureUnder chilling with ice
  2. distillationThe solvent was distilled off under reduced pressure
  3. temperatureThe mixtrue was refluxed
  4. temperatureunder heating for 14.5 hours
  5. distillationThe solvent was distilled off under reduced pressure
  6. additionThe residue was mixed with 10 ml of dichloromethane and 10 ml of water
  7. customto give
  8. customseparated layers
  9. filtrationfiltered
  10. customto remove insolubles
  11. washThe organic solvent portion was washed with water
  12. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  13. distillationto distill off the solvent
  14. customTheresidue was purified over a silica gel column

Sources & evidence

ORD record
ord-1073574015cd432395fa9fb5c5762b89
Source dataset
uspto-grants-1995_08
Patent number
US05446146

Reaction notes

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