Piperazine → Piperazine,1-[4-(4-chlorophenyl)butyl]-

HRID 4320

Reaction equation

HRID 4320 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11]Cl)=[CH:4][CH:3]=1.[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 200827321-Chloro-4-(4-chlorobutyl)benzene

Product 1

HCID 14097058Piperazine,1-[4-(4-chlorophenyl)butyl]-Yield 46.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 26.4 g of 4-(4-chlorophenyl)butyl chloride, 86.1 g of anhydrous piperazine and 250 ml of reagent ethanol was refluxed overnight. Solvent was evaporated from the product and the residue was chromatographed twice on silica with the eluant being CH2Cl2 /CH3OH/ammonium hydroxide (45:5:1). The first chromatography removed the bulk of the excess piperazine, the second provided 15.2 g of 1-[4-(4-chlorophenyl)butyl]piperazine as a colorless oil which solidified on standing (m.p. 139°-145° C.).

Workup

  1. temperaturewas refluxed overnight
  2. customSolvent was evaporated from the product
  3. customthe residue was chromatographed twice on silica with the eluant
  4. customThe first chromatography removed the bulk of the excess piperazine

Sources & evidence

ORD record
ord-81005d9a5e474ae9811ee087317133f2
Source dataset
uspto-grants-1988_02
Patent number
US04725597

Linked notes

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