Acetic Acid → HCID 9835825, compound

HRID 1790398Notes

Reaction equation

HRID 1790398 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]2)=[CH:13][CH:12]=1.C(O)(=O)C.ClC(Cl)C>C(OCC)(=O)C>[F:10][C:11]1[CH:12]=[CH:13][C:14]([N:17]2[CH2:22][CH2:21][CH:20]([N:1]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH2:3][CH2:2]3)[CH2:19][CH2:18]2)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 10328IndolineHCID 6062841-(4-fluorophenyl)piperidin-4-one

Product 1

HCID 9835825HCID 9835825, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Triacetoxylated sodium borohydride (760 mg) was added to a mixture of indoline (300 mg), 1-(4-fluorophenyl)-4-piperidone (580 mg), acetic acid (650 mg) and dichloroethane (30 ml), and the mixture was stirred for 2 hr. The obtained reaction solution was mixed with ethyl acetate and a saturated aqueous solution of sodium bicarbonate and the layers were separated. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate system) to give the title compound (470 mg) as white prismatic crystals (yield: 63%).

Workup

  1. customThe obtained reaction solution
  2. customa saturated aqueous solution of sodium bicarbonate and the layers were separated
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-d26a1681126c47aaacdd07b2c0719e47
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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