Pyrrolidine → Z-4-[4-chloro-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 504541Notes

Reaction equation

HRID 504541 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[CH:21]=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:23][C:24]1[CH:32]=[C:31]2[C:27]([CH2:28][C:29](=[O:33])[NH:30]2)=[CH:26][CH:25]=1.N1CCCC1>CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2/[CH:21]=[C:28]2\[C:29](=[O:33])[NH:30][C:31]3[C:27]\2=[CH:26][CH:25]=[C:24]([Cl:23])[CH:32]=3)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 11529912tert-butyl 4-(4-chloro-2-formylphenyl)tetrahydro-1(2H)-pyrazinecarboxylate

Product 1

HCID 86632079Z-4-[4-chloro-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl esterYield 92.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a manner similar to the method described in Example 1b, 4-(4-chloro-2-formyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (8 g, 25 mmol) was reacted with 6-chlorooxindole (4.1 g, 25 mmol) and pyrrolidine (1.8 g, 25 mmol) in methanol (50 mL) to give the title compound as a yellow solid (11 g).

Sources & evidence

ORD record
ord-a60c2a01f5e54dbb93e3ddcb9b2a713b
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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