Chlorosuccinimide → 1-(2-Chloro-5-methoxyphenyl)piperazine hydrochloride

HRID 270775Notes

Reaction equation

HRID 270775 reaction equation
[ClH:1].Cl.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:8]=[CH:9][CH:10]=1.[Cl:17]N1C(=O)CCC1=O>C(O)(=O)C.O>[ClH:17].[Cl:1][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH3:3])=[CH:6][C:7]=1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 814291-(3-Methoxyphenyl)piperazine dihydrochloride

Product 1

HCID 210709731-(2-Chloro-5-methoxyphenyl)piperazine hydrochloride

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 5.3 g (20 mmol) of 1-(3-Methoxyphenyl)piperazine dihydrochloride in 120 mL of acetic acid and 30 mL of water at 0° C. was added 3.3 g (20 mmol) of N-chlorosuccinimide. After 5 hours, 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) 7.28 (d, 1H), 6.66 (m, 3H), 3.70 (s, 3H), 3.32 (m, 4H), 3.20 (m, 4H) 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-64425cb3cfb44c05acc64284053568d5
Source dataset
uspto-grants-2008_11
Patent number
US07449576B1

Reaction notes

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