Chlorosuccinimide → 1-(2,4-Dichloro-5-methoxy-phenyl)-piperazine hydrochloride

HRID 1371996Notes

Reaction equation

HRID 1371996 reaction equation
[ClH:1].[ClH:2].[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]=[C:10]([Cl:2])[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 210709721-(2,4-Dichloro-5-methoxy-phenyl)-piperazine hydrochloride

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 530 mg (2.0 mmol) of 1-(3-Methoxyphenyl)piperazine dihydrochloride in 7 mL of acetic acid and 4 mL of water at 0° C. was added 700 mg (4.4 mmol) of N-chlorosuccinimide. The reaction was taken out of the ice/water bath after 2 hours, and allowed to stir overnight. After 12 hours, the reaction was concentrated to an oil in vacuo, and the oil was partitioned between ether and water. The phases were separated, the aqueous was basified with 1M NaOH, and was extracted with ethyl acetate. 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, the solution was acidified with 5M HCl in isopropanol and was diluted with ethyl acetate to effect crystallization. The product was isolated by filtration. 1H NMR (D2O, 400 MHz) 7.38 (s, 1H), 6.72 (s, 1H), 3.78 (s, 3H), 3.32 (m, 4H), 3.19 (m, 4H) ppm.

Workup

  1. waitAfter 12 hours
  2. concentrationthe reaction was concentrated to an oil in vacuo
  3. customthe oil was partitioned between ether and water
  4. customThe phases were separated
  5. extractionwas extracted with ethyl acetate
  6. washThe ethyl acetate phase was washed once each with water and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated to an oil in vacuo
  10. dissolutionThe oil was dissolved in a minimum volume of methanol
  11. additionwas diluted with ethyl acetate
  12. customcrystallization
  13. customThe product was isolated by filtration

Sources & evidence

ORD record
ord-1e70634d77304e2daa7acc24a4183513
Source dataset
uspto-grants-2007_01
Patent number
US07157464B2

Reaction notes

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