Piperazine → HCID 22313131, compound

HRID 1263475Notes

Reaction equation

HRID 1263475 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.O.Cl.Cl.N1CCNCC1.[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][Cl:22])=[CH:19][CH:18]=1>C(O)C>[Cl-:22].[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][N:1]2[CH2:6][CH2:5][NH2+:4][CH2:3][CH2:2]2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 96024-Fluorobenzyl chlorideHCID 12197850Piperazine-hydrogen chloride-water (1:2:1)

Product 1

HCID 22313131HCID 22313131, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 2.154 g(25 mM) of piperazine in 25 mL of absolute ethanol, was warmed in a bath at 65° C. Piperazine dihydrochloride hydrate (3.9765 g(25 mM)) was dissolved in the solution, by swirling. In the bath at 65° C. 3.6145 g(25 mM) of 4-fluorobenzyl chloride was added to the solution with vigorous stirring. The separation of white needles commenced almost immediately. After the solution had been stirred for an additional 25 minutes at 65° C., it was cooled, and the unstirred solution was kept in an ice bath for about 30 minutes. The crystals of piperazine dihydrochloride hydrate were collected by suction filtration, washed with three 5 mL portions of ice-cold absolute ethanol, and then dried. Approximately 3.989g(100.3%) of the dihydrochloride was recovered. Filtrate from this solution was evaporated to dryness at reduced pressure and crude 1-(4-methoxybenzyl)-4-piperazinium chloride was left as a residue. For removal of any piperazine dihydrochloride, the chloride may be crystallized after rapidly filtering a hot solution in about 20 mL of absolute ethanol. Concentration of the filtrate followed by cooling gave 5.248 g(91%) of 1-(4-fluorobenzyl)-4-piperazinium chloride.

Workup

  1. customat 65° C
  2. customThe separation of white needles
  3. temperatureit was cooled
  4. waitthe unstirred solution was kept in an ice bath for about 30 minutes
  5. filtrationThe crystals of piperazine dihydrochloride hydrate were collected by suction filtration
  6. washwashed with three 5 mL portions of ice-cold absolute ethanol
  7. customdried
  8. customApproximately 3.989g(100.3%) of the dihydrochloride was recovered
  9. customFiltrate from this solution was evaporated to dryness at reduced pressure and crude 1-(4-methoxybenzyl)-4-piperazinium chloride
  10. waitwas left as a residue
  11. customFor removal of any piperazine dihydrochloride
  12. customthe chloride may be crystallized
  13. filtrationafter rapidly filtering a hot solution in about 20 mL of absolute ethanol
  14. temperatureby cooling

Sources & evidence

ORD record
ord-32f6f3c44edf4c4ebc91ecb2dd9b15ac
Source dataset
uspto-grants-2003_04
Patent number
US06541479B1

Reaction notes

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