Piperazine → 1-(3-(Phenylthio)propyl)piperazine

HRID 435110Notes

Reaction equation

HRID 435110 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:7]1([S:13][CH2:14][CH2:15][CH2:16]Cl)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[Na+]>>[C:7]1([S:13][CH2:14][CH2:15][CH2:16][N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 4837PiperazineHCID 14798Sodium HydroxideHCID 2696063-Chloropropyl phenyl sulfide

Product 1

HCID 21954921-(3-(Phenylthio)propyl)piperazine

Procedure

To 1 liter 50% aqueous alcohol are added 3 moles piperazine, 1 mole 3-phenylthio-1-chloropropane, 1 mole 10N sodium hydroxide. The mixture is refluxed for 24 hours, with stirring. The methanol is then evaporated off, and the resulting material is extracted with methylene chloride. The organic phase is thoroughly washed with water, and is then concentrated and distilled, to give 1-(3-phenylthiopropyl)piperazine, bp0.5 mm =140°-142° C.

Workup

  1. temperatureThe mixture is refluxed for 24 hours
  2. customThe methanol is then evaporated off
  3. extractionthe resulting material is extracted with methylene chloride
  4. washThe organic phase is thoroughly washed with water
  5. concentrationis then concentrated
  6. distillationdistilled

Sources & evidence

ORD record
ord-e1b6f08d46954fc580901da766fb1ec3
Source dataset
uspto-grants-1983_08
Patent number
US04400381

Reaction notes

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