HCID 14931744, compound → 1-[4-(5-Nitro-1H-indol-3-yl)piperidin-1-yl]ethan-1-one
Reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=3)[NH:12][CH2:11]2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]>[O-2].[O-2].[Mn+4].[N+](C1C=CC=CC=1)([O-])=O>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=3)[NH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 150 °C
Procedure
A mixture of 3-(1-acetyl-4-piperidyl)-5-nitroindoline (10.0 g), manganese dioxide (17 g) and nitrobenzene (100 ml) was heated at 150° C. for 1 hour, with nitrogen gas being bubbled into the reaction mixture. The reaction mixture was cooled and the insoluble material was filtered off. The residue was washed with a mixture of chloroform and methanol (10:1 V/V) and the washings and the filtrate were combined and concentrated. The residue was dissolved in a mixture of chloroform and methanol (400 ml, 1:1 V/V) and the insoluble material was filtered off. The filtrate was concentrated to give 3-(1-acetyl-4-piperidyl)-5-nitroindole (4.67 g).
Workup
- custombeing bubbled into the reaction mixture
- temperatureThe reaction mixture was cooled
- filtrationthe insoluble material was filtered off
- washThe residue was washed with a mixture of chloroform and methanol (10:1 V/V)
- concentrationconcentrated
- dissolutionThe residue was dissolved in a mixture of chloroform and methanol (400 ml, 1:1 V/V)
- filtrationthe insoluble material was filtered off
- concentrationThe filtrate was concentrated
Sources & evidence
- ORD record
- ord-ae3ec5282fc540d29b0d8332671c55a8
- Source dataset
- uspto-grants-1988_05
- Patent number
- US04742057
Reaction notes
Loading…