1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-[(n-propylcarbamoyl)methyl]indoline → 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-(ethylcarbamoylmethyl)indole

HRID 1790502Notes

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][CH2:26][CH2:27]C)[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

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[(n-propylcarbamoyl)methyl]indoline (0.04 g) obtained in Example 150 and active manganese dioxide (0.08 g) in chloroform (30 ml) was vigorously stirred at 50° C. overnight. 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 white needles (yield: 84.6%).

Workup

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

Sources & evidence

ORD record: ord-7997046f50a54e64aea1dc32d4734df7
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07071201B2

Reaction notes

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