Rac-4-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1h-indol-3-yl]-piperazine-1-carboxylic acid tert-butyl ester → Rac-6-chloro-3-(3-chloro-benzyl)-3-piperazin-1-yl-1,3-dihydro-indol-2-one

HRID 556460Notes

Reaction equation

HRID 556460 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=3)[C:22]3[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=3)[NH:16][C:15]2=[O:24])[CH2:10][CH2:9]1)=O)(C)(C)C>FC(F)(F)C(O)=O>[Cl:23][C:19]1[CH:18]=[C:17]2[C:22]([C:14]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=3)([N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[C:15](=[O:24])[NH:16]2)=[CH:21][CH:20]=1

Participants

3

Reactant 1

HCID 57507308Rac-4-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1h-indol-3-yl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 24949934Rac-6-chloro-3-(3-chloro-benzyl)-3-piperazin-1-yl-1,3-dihydro-indol-2-oneYield 84.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The mixture of rac-4-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-piperazine-1-carboxylic acid tert-butyl ester (900 mg, 1.89 mmol) in trifluoroacetic acid (10 mL) was stirred at room temperature for 0.5 h. Then the solution was concentrated and extracted with dichloromethane. The organic layer was dried over Na2SO4, filtered and concentrated to give 0.6 g of rac-6-chloro-3-(3-chloro-benzyl)-3-piperazin-1-yl-1,3-dihydro-indol-2-one as a yellow solid. MS m/z 376 (M+H)+.

Workup

  1. concentrationThen the solution was concentrated
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-10a1352f61fa46b59c006cf0299dbc1d
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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