HCID 22038030, compound → 1-[1-(4-Acetamidomethylphenethyl)piperidin-4-yl]indole

HRID 1790495Notes

Reaction equation

HRID 1790495 reaction equation
[C:1]([NH:4][CH2:5][C:6]1[CH:28]=[CH:27][C:9]([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:20][CH2:19]3)[CH2:14][CH2:13]2)=[CH:8][CH:7]=1)(=[O:3])[CH3:2]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[C:1]([NH:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19]3)[CH2:14][CH2:13]2)=[CH:27][CH:28]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 22038030HCID 22038030, compound

Product 1

HCID 220384331-[1-(4-Acetamidomethylphenethyl)piperidin-4-yl]indoleYield 80.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

A suspension of 1-[1-(4-acetamidomethylphenethyl)piperidin-4-yl]indoline (0.80 g) obtained in Example 36 and active manganese dioxide (1.32 g) in chloroform (30 ml) was heated under reflux for 6 hr with vigorous stirring. Then the reaction mixtures were filtered through celite and the residue was washed with chloroform. The filtrate was concentrated under reduced pressure and the obtained residue was crystallized from a solvent mixture of ethyl acetate with hexane to give the title compound (0.64 g) as a white powder (yield: 80.4%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hr with vigorous stirring
  3. customThen the reaction mixtures
  4. filtrationwere filtered through celite
  5. washthe residue was washed with chloroform
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe obtained residue was crystallized from a solvent mixture of ethyl acetate with hexane

Sources & evidence

ORD record
ord-2189746554ae41daa699e07252619468
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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