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1-[1-(4-Fluorophenethyl)-piperidin-4-yl]-6-(cyclopropylcarbamoylmethyl)indoline → 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-(ethylcarbamoylmethyl)indole

HRID 1790500
Notes
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Reaction equation

HRID 1790500 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][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]([CH2:23][C:24](=[O:29])[NH:25][CH:26]5C[CH2:27]5)[CH:21]=4)[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[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](=[O:29])[NH:25][CH2:26][CH3:27])[CH:21]=4)[CH:16]=[CH:15]3)[CH2:12][CH2:13]2)=[CH:30][CH:31]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 220378941-[1-(4-Fluorophenethyl)-piperidin-4-yl]-6-(cyclopropylcarbamoylmethyl)indoline

Product 1

HCID 220383791-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-(ethylcarbamoylmethyl)indoleYield 81.9%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[(cyclopropylcarbamoyl)methyl]indoline (0.04 g) obtained in Example 154 and active manganese dioxide (0.04 g) in chloroform (30 ml) was vigorously stirred at 50° C. for 10 hr. Then the reaction mixtures were filtered through celite and the residue was washed with chloroform. After concentrating the filtrate under reduced pressure, the residue was recrystallized from chloroform/hexane to give the title compound (0.03 g) as a white powder (yield: 81.9%).

Workup

  1. customThen the reaction mixtures
  2. filtrationwere filtered through celite
  3. washthe residue was washed with chloroform
  4. concentrationAfter concentrating the filtrate under reduced pressure
  5. customthe residue was recrystallized from chloroform/hexane

Sources & evidence

ORD record
ord-16fb0e97fa884abab3ac689844bcc368
Source dataset
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07071201B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes