Piperazine → HCID 22760364, compound

HRID 1703788Notes

Reaction equation

HRID 1703788 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([CH:20](Cl)[CH3:21])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1>C1C=CC=CC=1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]([N:1]3[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]3)[CH3:21])=[CH:16][CH:15]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 14674270HCID 14674270, compound

Product 1

HCID 22760364HCID 22760364, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

While stirring, reflux a solution of 90g of anhydrous piperazine, 52g of 4'-chloro-4-(1-chloroethyl)[1,1']biphenyl and 700 ml of anhydrous benzene for 24 hours. Add 300 ml. of water to the reaction mixture, separate the benzene layer and extract with dilute hydrochloric acid. Separate and filter the acidic aqueous phase, basify the filtrate with dilute sodium hydroxide and extract with methylene chloride. Dry the organic extract, concentrate and triturate the resulting solid residue with petroleum ether. Filter and recrystallize the product from methanol to yield 1-[1-(4'-chloro[1,1']biphenyl-4-yl)ethyl] piperazine m.p. 164°-165° C. The dihydrochloride salt (from methanol as hemihydrate) has a m.p. 263°-264°.

Workup

  1. additionAdd 300 ml
  2. customof water to the reaction mixture, separate the benzene layer
  3. extractionextract with dilute hydrochloric acid
  4. customSeparate
  5. filtrationfilter the acidic aqueous phase
  6. extractionextract with methylene chloride
  7. customDry the organic extract
  8. concentrationconcentrate
  9. customtriturate the resulting solid residue with petroleum ether
  10. filtrationFilter
  11. customrecrystallize the product from methanol

Sources & evidence

ORD record
ord-5e091529b244447d904618e60bc12fbc
Source dataset
uspto-grants-1978_11
Patent number
US04125612

Reaction notes

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