Piperazine → Piperazine, 1-(phenylmethyl)-, hydrochloride (1:2)

HRID 2052806Notes

Reaction equation

HRID 2052806 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[OH-].[K+].[CH2:9]([Cl:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>[Br-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.O.C1C=CC=CC=1>[ClH:16].[ClH:16].[CH2:9]([N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 3

HCID 4837PiperazineHCID 7503Benzyl ChlorideHCID 14797Potassium Hydroxide

Product 1

HCID 12198046Piperazine, 1-(phenylmethyl)-, hydrochloride (1:2)Yield 55%

Reagents, catalysts & solvents 3

HCID 5974Hexadecyltrimethylammonium BromideCatalystHCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A mixture of piperazine (350 mmol), KOH (100 mmol) and hexadecyl-trimethyl ammonium bromide (CTAB, 1 mmol) in water (18 ml) was heated to get a solution. Thereafter, benzyl chloride (100 mmol) in 140 ml of benzene was added to the solution dropwise at 70° C., and refluxed for 1 h. The organic layer was washed with water and saline, dried (MgSO4), filtered and evaporated, the residue was dissolved by 50 ml of ethanol and adjusted to a PH of 2 by HCl/C2H5OH (5N), the resulting precipitate was recrystallized from ethanol to obtain N-benzyl piperazine dihydrochloride (55-86%).

Workup

  1. temperaturewas heated
  2. customto get a solution
  3. temperaturerefluxed for 1 h
  4. washThe organic layer was washed with water and saline
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. dissolutionthe residue was dissolved by 50 ml of ethanol
  9. customthe resulting precipitate was recrystallized from ethanol

Sources & evidence

ORD record
ord-3683190dea0e4fcfb9ee16547cfc9322
Source dataset
uspto-grants-2008_02
Patent number
US07326710B2

Reaction notes

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