Piperidine → HCID 66772455, compound

HRID 1645275Notes

Reaction equation

HRID 1645275 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[CH3:12][N:13]1[CH2:19][CH2:18][CH2:17][N:16]([C:20]([C:22]2[CH:27]=[CH:26][C:25]([C:28]3[O:32][C:31]([C:33](=O)[CH3:34])=[CH:30][CH:29]=3)=[CH:24][CH:23]=2)=[O:21])[CH2:15][CH2:14]1.N1CCCCC1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[C:33]([C:31]1[O:32][C:28]([C:25]2[CH:24]=[CH:23][C:22]([C:20]([N:16]3[CH2:17][CH2:18][CH2:19][N:13]([CH3:12])[CH2:14][CH2:15]3)=[O:21])=[CH:27][CH:26]=2)=[CH:29][CH:30]=1)[CH3:34]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 1528015-ChlorooxindoleHCID 59190116HCID 59190116, compound

Product 1

HCID 66772455HCID 66772455, compoundYield 19.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5-chlorooxindole (362 mg, 2.17 mmol), 1-(5-(4-(4-methyl-1,4-diazepane-1-carbonyl)phenyl)furan-2-yl)ethanone (800 mg of oil) and piperidine (214 μL, 2.17 mmol) in toluene (10 mL) was heated at reflux with a Dean-Stark receiver for 16 hours. After evaporation of the solvent, purification by silica column chromatography (methanol gradient in dichloromethane, 0 to 5% vol) gave 5-chloro-3-(1-(5-(4-(4-methyl-1,4-diazepane-1-carbonyl)phenyl)furan-2-yl)ethylidene)indolin-2-one (200 mg) as an E:Z mixture. LCMS (ES): m/z 476 [M+1]+.

Workup

  1. temperatureat reflux with a Dean-Stark receiver for 16 hours
  2. customAfter evaporation of the solvent, purification by silica column chromatography (methanol gradient in dichloromethane, 0 to 5% vol)

Sources & evidence

ORD record
ord-ffa4277f4a03491293b0e1b562333993
Source dataset
uspto-grants-2012_02
Patent number
US08124649B2

Reaction notes

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