Acetic Acid → HCID 53784335, compound

HRID 1420153Notes

Reaction equation

HRID 1420153 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH2:10][CH:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)[CH3:12])=[C:4]([N+:26]([O-])=O)[CH:3]=1.[C:29](O)(=O)[CH3:30]>[Zn]>[F:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]([CH2:9][CH2:10][CH:11]([N:13]3[CH2:18][CH2:17][N:16]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[CH2:15][CH2:14]3)[CH3:12])[C:29]([CH3:30])=[N:26][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 54174416HCID 54174416, compound

Product 1

HCID 53784335HCID 53784335, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

To a refluxing, stirred mixture of (4-fluoro-2-nitro-phenyl)-{3-[4-(4-fluorophenyl) piperazin-1-yl]-butyl}-amine (0.38 gm), 10 ml acetic acid are added small portions of Zn dust (excess) until a nearly colorless reaction mixture is obtained approx. 4 hours). Insolubles are removed by filtration, washed with acetic acid and the combined acetic acid layer concentrated to a black oil. This oily residue is dissolved in ethyl acetate (50 ml) and washed with 2×10 ml water and brine. The organic layer is collected, the sovent removed and the residue purified by flash chromatography (solid phase: SiO2 ; eluent: gradient starting with ethyl acetate followed by ethyl acetate/methanol 8:2). Obtained are 0.1 gm of 5-fluoro-1-{3-[4-(4-fluoro-phenyl)-piperazin-1-yl]-butyl}-2-1H-benzoimidazole. (M+/Z 384.47).

Workup

  1. customis obtained approx. 4 hours)
  2. customInsolubles are removed by filtration
  3. washwashed with acetic acid
  4. concentrationthe combined acetic acid layer concentrated to a black oil
  5. dissolutionThis oily residue is dissolved in ethyl acetate (50 ml)
  6. washwashed with 2×10 ml water and brine
  7. customThe organic layer is collected
  8. customthe sovent removed
  9. customthe residue purified by flash chromatography (solid phase: SiO2 ; eluent: gradient starting with ethyl acetate followed by ethyl acetate/methanol 8:2)
  10. customObtained

Sources & evidence

ORD record
ord-b9c27967f6e44af5958e9811baf4dd97
Source dataset
uspto-grants-1999_03
Patent number
US05889010

Reaction notes

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