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

HRID 1790500Notes

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

Participants

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

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

Reaction notes

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