Ammonium Chloride → 2,2,2-Trifluoro-1-{4-[2-methoxy-5-(naphthalene-1-sulfonyl)-phenyl]-piperazin-1-yl}-ethanone

HRID 2416666Notes

Reaction equation

HRID 2416666 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:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[CH2:15][CH2:14]1.[C:25]1([Mg]Br)[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1.[Cl-].[NH4+]>C1COCC1>[F:21][C:20]([F:23])([F:22])[C:19]([N:16]1[CH2:17][CH2:18][N:13]([C:4]2[CH:5]=[C:6]([S:9]([C:33]3[C:34]4[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH:30]=[CH:31][CH:32]=3)(=[O:11])=[O:10])[CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH2:14][CH2:15]1)=[O:24]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 121366554-Methoxy-3-[4-(2,2,2-trifluoro-acetyl)-piperazin-1-yl]-benzenesulfonyl chlorideHCID 178418298HCID 178418298, compound

Product 1

HCID 121366542,2,2-Trifluoro-1-{4-[2-methoxy-5-(naphthalene-1-sulfonyl)-phenyl]-piperazin-1-yl}-ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-methoxy-3-[4-(2,2,2-trifluoro-acetyl)-piperazin-1-yl]-benzenesulfonyl chloride (0.19 g; 0.5 mmol) in THF (0.5 mL) at 0° C. under argon atmosphere was added dropwise a solution of 1-naphthylmagnesium bromide in THF (0.5M, 2 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 and the residue was purified by column chromatography on silica gel (eluting with hexane-ethyl acetate (7:3, v/v) to give 2,2,2-trifluoro-1-{4-[2-methoxy-5-(naphthalene-1-sulfonyl)-phenyl]-piperazin-1-yl}-ethanone (1) as a white solid (0.110 g; 47%), MS, MH+ 479.

Workup

  1. extractionthe mixture was extracted into ethyl acetate (20 mL)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customthe residue was purified by column chromatography on silica gel (
  5. washeluting with hexane-ethyl acetate (7:3

Sources & evidence

ORD record
ord-4b1e2084164d425c935e7b25077bc250
Source dataset
uspto-grants-2004_11
Patent number
US06825202B2

Reaction notes

Loading…