3,4-Dichlorobenzyl chloride → 1-(3,4-Dichlorobenzyl)piperazine

HRID 1380515Notes

Reaction equation

HRID 1380515 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5]Cl.CCOC([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)=O.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[K+]>C(O)C.C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 76093,4-Dichlorobenzyl chlorideHCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 10340Sodium CarbonateHCID 14797Potassium Hydroxide

Product 1

HCID 27580741-(3,4-Dichlorobenzyl)piperazineYield 19%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 7237O-XyleneSolvent

Procedure

A mixture of 39.0 g (0.2 moles) of 3,4-dichlorobenzyl chloride, 31.6 g (0.2 moles) of ethyl N-piperazinocarboxylate, 22.0 g (0.21 moles) of anhydrous sodium carbonate and 200 ml of xylene was refluxed for 3 hours using a Dean-Stark trap. Then the mixture was stirred at room temperature for 16 hours, filtered and washed with xylene. The filtrate was evaporated in vacuo to give a syrup. A 750 ml amount of 4N potassium hydroxide in 95% ethanol was added to the syrup and the mixture was refluxed for 18 hours. The reaction mixture was evaporated to a paste and 250 ml of water was added. The solution was extracted twice with 250 ml of chloroform. The extracts were combined, dried over magnesium sulfate and filtered. The filtrate was evaporated in vacuo and gave a syrup. The syrup was distilled, bp 132°-135° C./0.05 mm of mercury and gave 9.3 g of 1-(3,4-dichlorobenzyl)piperazine as a colorless liquid.

Workup

  1. temperaturewas refluxed for 3 hours
  2. filtrationfiltered
  3. washwashed with xylene
  4. customThe filtrate was evaporated in vacuo
  5. customto give a syrup
  6. temperaturethe mixture was refluxed for 18 hours
  7. customThe reaction mixture was evaporated to a paste and 250 ml of water
  8. additionwas added
  9. extractionThe solution was extracted twice with 250 ml of chloroform
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. customThe filtrate was evaporated in vacuo
  13. customgave a syrup
  14. distillationThe syrup was distilled

Sources & evidence

ORD record
ord-78034706accc4d2fbc06d2b923f5f634
Source dataset
uspto-grants-1986_04
Patent number
US04582833

Reaction notes

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