Ammonium Chloride → 1-[5-(4-Fluoro-naphthalene-1-sulfonyl)2-methoxyphenyl] piperazine

HRID 2416671Notes

Reaction equation

HRID 2416671 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][C:4]=1[N:13]1[CH2:18][CH2:17][N:16](C(=O)C(F)(F)F)[CH2:15][CH2:14]1.[F:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]([Mg]Br)=[CH:28][CH:27]=1.[Cl-].[NH4+]>C1COCC1>[F:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]([S:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([N:13]3[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]3)[CH:5]=2)(=[O:10])=[O:11])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 121366554-Methoxy-3-[4-(2,2,2-trifluoro-acetyl)-piperazin-1-yl]-benzenesulfonyl chlorideHCID 178505833HCID 178505833, compound

Product 1

HCID 101356191-[5-(4-Fluoro-naphthalene-1-sulfonyl)2-methoxyphenyl] piperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-methoxy-3-[4-(2,2,2-trifluoro-acetyl)piperazin-1-yl]bezenesulfonyl chloride (0.19 g; 0.5 mmol), prepared as in Example 1 Step 2, in THF (0.5 mL) at ambient temperature under argon atmosphere was added dropwise a solution of 4-fluoro-1-naphthylmagnesium bromide in THF (0.25 M, 4 mL; 1 mmol). After stirring at this temperature for 1 h a saturated solution of ammonium chloride was added and the mixture was extracted into ethyl acetate (20 mL). The organic phase was dried (Na2SO4) and concentrated in vacuo .The residue was dissolved in dioxane (2 mL) and a solution of 6N NaOH (0.5 mL) was added. After stirring at ambient temperature for 1 h water was added (10 ml) and the mixture was extracted into ethyl acetate (20 ml). The organic phase was extracted into 2N aqueous HCl. The aqueous layer was adjusted with 6N NaOH solution to pH 14 and extracted with ethyl acetate. The organic phase was dried (Na2SO4) and concentrated in vacuo to give the 1-[5-(4-fluoro-naphthalene-1-sulfonyl)2-methoxyphenyl]piperazine (401) as a white solid (0.060 g; 30%). The hydrochloride salt was prepared from ethanol-hydrogen chloride, m. p. 155.0-159.0° C.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted into ethyl acetate (20 mL)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated in vacuo .The residue
  5. dissolutionwas dissolved in dioxane (2 mL)
  6. additiona solution of 6N NaOH (0.5 mL) was added
  7. additionwas added (10 ml)
  8. extractionthe mixture was extracted into ethyl acetate (20 ml)
  9. extractionThe organic phase was extracted into 2N aqueous HCl
  10. extractionextracted with ethyl acetate
  11. dry with materialThe organic phase was dried (Na2SO4)
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-42c7a8beb35a4351a7e3fb6260c99c9c
Source dataset
uspto-grants-2004_11
Patent number
US06825202B2

Reaction notes

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