Piperidine → Z-2-[4-chloro-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-2-methyl-propionic acid tert-butyl ester

HRID 1512039Notes

Reaction equation

HRID 1512039 reaction equation
[C:1]([O:5][C:6](=[O:20])[C:7]([O:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[CH:18]=O)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[Cl:21][C:22]1[CH:30]=[C:29]2[C:25]([CH2:26][C:27](=[O:31])[NH:28]2)=[CH:24][CH:23]=1.N1CCCCC1>CO>[C:1]([O:5][C:6](=[O:20])[C:7]([O:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1/[CH:18]=[C:26]1\[C:27](=[O:31])[NH:28][C:29]2[C:25]\1=[CH:24][CH:23]=[C:22]([Cl:21])[CH:30]=2)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 575662212-(4-Chloro-2-formyl-phenoxy)-2-methyl-propionic acid tert-butyl ester

Product 1

HCID 68757836Z-2-[4-chloro-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-2-methyl-propionic acid tert-butyl esterYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 2-(4-chloro-2-formyl-phenoxy)-2-methyl-propionic acid tert-butyl ester (5.17 g, 17.3 mmol) and 6-chlorooxindole (2.89 g, 17.3 mmol) were anhydrous methanol (100 mL) at room temperature was slowly added piperidine (1.7 mL, 17.3 mmol). The reaction mixture was heated at 70° C. for 0.5 h. Then the mixture was cooled to room temperature and filtered. The precipitate was dried and collected to give E/Z-2-[4-chloro-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-2-methyl-propionic acid tert-butyl ester as a yellow solid (Yield 6.5 g, 84%).

Workup

  1. customat room temperature
  2. temperatureThen the mixture was cooled to room temperature
  3. filtrationfiltered
  4. customThe precipitate was dried
  5. customcollected

Sources & evidence

ORD record
ord-2ac93561c61a4e70837cc8dfd58fc651
Source dataset
uspto-grants-2012_07
Patent number
US08217051B2

Reaction notes

Loading…