Dichloromethane → N-[2-(5-bromo-1-indolinyl)-5-bromophenyl]-4-methyl-1-piperazinecarboxamide

HRID 978291Notes

Reaction equation

HRID 978291 reaction equation
[Br:1]N1C(=O)CCC1=O.[N:9]1([C:18]2[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:19]=2[NH:25][C:26]([N:28]2[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]2)=[O:27])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10]1.ClCCl>CN(C)C=O>[Br:1][C:14]1[CH:13]=[C:12]2[C:17](=[CH:16][CH:15]=1)[N:9]([C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:19]=1[NH:25][C:26]([N:28]1[CH2:29][CH2:30][N:31]([CH3:34])[CH2:32][CH2:33]1)=[O:27])[CH2:10][CH2:11]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 13823352N-[2-(indolin-1-yl)-5-bromophenyl]-4-methyl-1-piperazinecarboxamide

Product 1

HCID 13823368N-[2-(5-bromo-1-indolinyl)-5-bromophenyl]-4-methyl-1-piperazinecarboxamideYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

N-Bromosuccinimide (2.6 g, 14.5 mmoles) was added to a solution of N-[2-(indolin-1-yl)-5-bromophenyl]-4-methyl-1-piperazinecarboxamide (5.0 g, 12.0 mmoles) in dimethylformamide (50 ml). The solution was stirred at room temperature for 15 minutes and at 60° C. for 15 minutes. The solution was cooled and poured into dichloromethane (500 ml). The layers were separated and the organic phase was washed with water (3×500 ml), brine (500 ml), and dried over anhydrous sodium sulfate. The mixture was filtered and the filtrate was concentrated. The residue was purified by chromatography over silica gel (60 g, eluted with 4% methanol:96% dichloromethane, 1 l). The appropriate fractions were pooled and concentrated to give 4.8 g (84%) of product. Recrystallization from chloroform and hexane gave the analytical sample, mp 118°-119.5° C.

Workup

  1. temperatureThe solution was cooled
  2. customThe layers were separated
  3. washthe organic phase was washed with water (3×500 ml), brine (500 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by chromatography over silica gel (60 g, eluted with 4% methanol:96% dichloromethane, 1 l)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-13cded9283724d43a2ce200543539a2f
Source dataset
uspto-grants-1987_05
Patent number
US04663453

Reaction notes

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