Bromine → 1-(4-Bromo-3-methylphenyl)piperazine hydrochloride

HRID 270774Notes

Reaction equation

HRID 270774 reaction equation
[ClH:1].Cl.[CH3:3][C:4]1[CH:5]=[C:6]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1.[Br:16]Br>C(O)(=O)C.O>[ClH:1].[Br:16][C:9]1[CH:8]=[CH:7][C:6]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:5][C:4]=1[CH3:3]

Participants

5

Reactant 2

HCID 24408BromineHCID 831101-(m-Tolyl)piperazine dihydrochloride

Product 1

HCID 210710171-(4-Bromo-3-methylphenyl)piperazine hydrochloride

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 966 mg (4.0 mmol) of 1-(3-Methylphenyl)piperazine dihydrochloride in 9 mL of acetic acid and 1 mL of water at 0° C. was added 640 mg (4.0 mmol) of bromine. After 1 hour, the reaction was concentrated to an oil in vacuo, and the oil was partitioned between ethyl acetate and 1M NaOH. The phases were separated, and the ethyl acetate phase was washed once each with water and brine, dried over Na2SO4, filtered, and the filtrate was concentrated to an oil in vacuo. The oil was dissolved in a minimum volume of methanol, and the solution was acidified with 2M HCl in ether. The product was isolated by filtration. 1H NMR (D2O, 400 MHz) 7.37 (d, 1H), 6.85 (s, 1H), 6.76 (d, 1H), 3.37 (m, 8H), 2.17 (s, 3H) ppm.

Workup

  1. concentrationthe reaction was concentrated to an oil in vacuo
  2. customthe oil was partitioned between ethyl acetate and 1M NaOH
  3. customThe phases were separated
  4. washthe ethyl acetate phase was washed once each with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated to an oil in vacuo
  8. dissolutionThe oil was dissolved in a minimum volume of methanol
  9. customThe product was isolated by filtration

Sources & evidence

ORD record
ord-5226836a7cac4febaeab73ccd0b675cd
Source dataset
uspto-grants-2008_11
Patent number
US07449576B1

Reaction notes

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