1-Methylpiperazine → N-[2-(5-bromo-1-indolinyl)phenyl]-4-methyl-1-piperazinecarboxamide

HRID 4083Notes

Reaction equation

HRID 4083 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17](C1C=CC=CC=1)[C:18](=O)[O-:19])[CH2:6][CH2:5]2.[CH3:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>CCOCC>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH:17][C:18]([N:31]1[CH2:32][CH2:33][N:28]([CH3:27])[CH2:29][CH2:30]1)=[O:19])[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 131715128N-[2-(5-bromo-1-indolinyl)phenyl]phenylcarbamate

Product 1

HCID 13823366N-[2-(5-bromo-1-indolinyl)phenyl]-4-methyl-1-piperazinecarboxamideYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of N-[2-(5-bromo-1-indolinyl)phenyl]phenylcarbamate (11.5 g, 28.5 mmoles), N-methylpiperazine (15 ml) and ether (50 ml) was stirred at room temperature for 2 hours. The ether was evaporated. The mixture was filtered through a silica gel column (150 g), packed with dichloromethaane, and the column was washed with 2% methanol-dichloromethane solution (2 l). The solvent was evaporated. The residue was purified by flash chromatography on a silica gel column (150 g, 230-400 mesh), eluted with 1% methanol/dichloromethane (4 l), 1.5% methanol/dichloromethane (2 l), and 2% methanol/dichloromethane. The fractions containing the desired material were collected and evaporated to give 10.9 g (90%) of product. Crystallization from chloroform and hexane afforded the analytical sample, mp 108°-110° C.

Workup

  1. customThe ether was evaporated
  2. filtrationThe mixture was filtered through a silica gel column (150 g)
  3. washthe column was washed with 2% methanol-dichloromethane solution (2 l)
  4. customThe solvent was evaporated
  5. customThe residue was purified by flash chromatography on a silica gel column (150 g, 230-400 mesh)
  6. washeluted with 1% methanol/dichloromethane (4 l), 1.5% methanol/dichloromethane (2 l), and 2% methanol/dichloromethane
  7. additionThe fractions containing the desired material
  8. customwere collected
  9. customevaporated

Sources & evidence

ORD record
ord-acd7ac4d5a5744caa39dbf8193533fd0
Source dataset
uspto-grants-1988_02
Patent number
US04723003

Reaction notes

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