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

HRID 2416671노트

반응식

HRID 2416671 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-42c7a8beb35a4351a7e3fb6260c99c9c
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06825202B2

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