Piperazine → 1-[3-(Dimethylamino)propyl]piperazine

HRID 542839Notes

Reaction equation

HRID 542839 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl.Cl[CH2:9][CH2:10][CH2:11][N:12]([CH3:14])[CH3:13].C(=O)(O)[O-].[Na+]>C(O)C>[CH3:13][N:12]([CH3:14])[CH2:11][CH2:10][CH2:9][N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 27362341-[3-(Dimethylamino)propyl]piperazineYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 100 g (1.2 mole) of piperazine, 72 g (0.455 mole) of 3-chloro-N,N-dimethylpropanamine, hydrochloride and 110 g (1.3 mole) of sodium bicarbonate in 500 ml of ethanol was heated under reflux for 7 hr, allowed to cool, filtered and concentrated to dryness under vacuum. The concentrate was slurried in dichloromethane and filtered. The filterate was concentrated and then distilled under water pump pressure (~5 mm) to afford 34 g (44%) of the desired product, bp 100°-102°/5 mm.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 7 hr
  3. temperatureto cool
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under vacuum
  6. filtrationfiltered
  7. concentrationThe filterate was concentrated
  8. distillationdistilled under water pump pressure (~5 mm)

Sources & evidence

ORD record
ord-5c83ee8df2e24f69b937c121f736f581
Source dataset
uspto-grants-1987_04
Patent number
US04659708

Reaction notes

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