Water → HCID 22038151, compound

HRID 1790497Notes

Reaction equation

HRID 1790497 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][CH2:7][N:8]2[CH2:14][CH2:13][CH2:12][CH:11]([N:15]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=4)[C:18](=O)[C:16]3=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.O>O1CCCC1>[F:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][CH2:7][N:8]2[CH2:14][CH2:13][CH2:12][CH:11]([N:15]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=4)[CH:18]=[CH:16]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 962WaterHCID 22038146HCID 22038146, compound

Product 1

HCID 22038151HCID 22038151, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-(4-Fluorophenethyl)-4-(6-methoxyisatin-1-yl)homopiperidine (0.4 g) was dissolved in tetrahydrofuran (1.0 ml). Under nitrogen atmosphere, a 2.0 M solution (4.0 ml) of borane-tetrahydrofuran complex in tetrahydrofuran was added dropwise thereinto in a water bath followed by heating under reflux for 3 hr. The reaction solution was ice cooled and water was added thereto. Next, the reaction solution was partitioned between water and ethyl acetate and the organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in pyridine (5.0 ml) and stirred at room temperature for 11 hr. After adding water, the reaction solution was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Then the resulting residue was purified by NH-silica gel column chromatography (hexane/ethyl acetate system) to give 1-(4-florophenethyl)-4-(6-methoxyindol-1-yl)homopiperidine as a yellow oil. Then this product was treated as in Production Example 64 to give the free title compound (0.095g) asayellowoil (yield: 27.2%).

Workup

  1. customin a water bath followed
  2. temperatureby heating
  3. temperatureunder reflux for 3 hr
  4. temperaturecooled
  5. customNext, the reaction solution was partitioned between water and ethyl acetate
  6. washthe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. dissolutionThe residue was dissolved in pyridine (5.0 ml)
  10. additionAfter adding water
  11. customthe reaction solution was partitioned between water and ethyl acetate
  12. washThe organic layer was washed with brine
  13. dry with materialdried over anhydrous magnesium sulfate
  14. concentrationconcentrated under reduced pressure
  15. customThen the resulting residue was purified by NH-silica gel column chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-34eee7181b7f4acfbea646de6deb5eee
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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