Hydrochloric Acid → HCID 21963613, compound

HRID 2211849Notes

Reaction equation

HRID 2211849 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Cl)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].Cl>C(#N)C.C(O)(C)C.CCOCC.O>[ClH:1].[ClH:14].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:19][C:18]3[CH:21]=[CH:22][C:15]([Cl:14])=[CH:16][CH:17]=3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 11430Potassium CarbonateHCID 974781-(4-Chlorophenyl)piperazine

Product 1

HCID 21963613HCID 21963613, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 3776IsopropanolSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(4-chlorophenyl)piperazine (1.61 g, 0.01 mole), 4-chlorobenzyl chloride (2.10 g, 0.01 mole) and potassium carbonate (2 g) in acetonitrile (40 mL) is heated at reflux for 6 hours under a nitrogen atmosphere. After cooling, the reaction mixture is poured into water (50 mL) and ether (50 mL). The aqueous layer is discarded and the organic layer is extracted with 1 N aqueous hydrochloric acid solution. The acidic extract is neutralized with 6 N ammonium hydoxide solution and extracted with ether. The organic layer is dried (Na2SO4) and concentrated to provide the crude free base of the desired unsymmetrically substituted piperazine. This material is dissolved in warm isopropanol (10 mL) and treated with a 1 N solution of HCl in ether until acidic to pH paper. Upon cooling, crystals of dihydrochloride salt are collected (2.2 g, 56%).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 6 hours under a nitrogen atmosphere
  3. temperatureAfter cooling
  4. extractionthe organic layer is extracted with 1 N aqueous hydrochloric acid solution
  5. extractionThe acidic extract
  6. extractionextracted with ether
  7. dry with materialThe organic layer is dried (Na2SO4)
  8. concentrationconcentrated
  9. customto provide the crude free base of the
  10. temperatureUpon cooling
  11. customcrystals of dihydrochloride salt are collected (2.2 g, 56%)

Sources & evidence

ORD record
ord-9504d95ea5a746f7ba1ac2faf80e3eb9
Source dataset
uspto-grants-2006_09
Patent number
US07101887B2

Reaction notes

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