Hydrochloric Acid → HCID 22038143, compound

HRID 1790465Notes

Reaction equation

HRID 1790465 reaction equation
[F:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([CH:23](O)[C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=5)[CH:21]=4)[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl>C(O)C.[C].[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][CH:11]([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([CH2:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=5)[CH:21]=4)[CH2:16][CH2:15]3)[CH2:12][CH2:13]2)=[CH:31][CH:32]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22037901HCID 22037901, compound

Product 1

HCID 22038143HCID 22038143, compoundYield 24.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-[1-hydroxy-1-(2-pyridyl)methyl]indoline (0.321 g) was dissolved in ethanol (86.4 ml) f ollowed by the addition of 1 N hydrochloric acid (3.7 ml) and palladium carbon. Then the resultant mixture was catalytically reduced under atmospheric pressure for 3 hr. After filtering off the catalyst, the filtrate was concentrated under reduced pressure. To the residue were added a saturated aqueous solution of sodium bicarbonate and ethyl acetate and the layers were separated. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Then the residue was purified by NH-silica gel column chromatography (hexane/ethyl acetate-methanol system) to give the title compound (0.076 g) as ayellow oil (yield: 24.6%).

Workup

  1. filtrationAfter filtering off the catalyst
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the residue were added a saturated aqueous solution of sodium bicarbonate and ethyl acetate
  4. customthe layers were separated
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThen the residue was purified by NH-silica gel column chromatography (hexane/ethyl acetate-methanol system)

Sources & evidence

ORD record
ord-d5f63a48d4ca4b87914def778f1304f4
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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