Aniline → HCID 16128424, compound

HRID 747097Notes

Reaction equation

HRID 747097 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([C:11](=[O:29])[C:12]([N:14]1[CH2:19][CH2:18][N:17]([CH:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)C#N)[CH2:16][CH2:15]1)=[O:13])=[CH:5][NH:6]2.[NH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CN(C=O)C.O=[Mn]=O>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([C:11](=[O:29])[C:12]([N:14]1[CH2:15][CH2:16][N:17]([C:20]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[N:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:18][CH2:19]1)=[O:13])=[CH:5][NH:6]2

Participants

5

Reactant 2

HCID 6115AnilineHCID 58852054HCID 58852054, compound

Product 1

HCID 16128424HCID 16128424, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6228DimethylformamideSolvent

Procedure

An excess amount of MnO2 (500 mg) was added into a solution of 2-(4-(2-(4-fluoro-1H-indol-3-yl)-2-oxoacetyl)piperazin-1-yl)-2-phenylacetonitrile (100 mg) and aniline (0.5 ml) in DMF (10 ml), and the reaction was kept stirring for 2 days. The solids were removed by filtration. The filtrate was concentrated under vaccum to give a residure which was purified by using Shimadzu automated preparative HPLC System to afford 1-(4-fluoro-1H-indol-3-yl)-2-(4-(phenyl(phenylimino)methyl)piperazin-1-yl)ethane-1,2-dione.

Workup

  1. customThe solids were removed by filtration
  2. concentrationThe filtrate was concentrated under vaccum
  3. customto give a residure which
  4. customwas purified

Sources & evidence

ORD record
ord-4ca9b99439a04457945ae5f3aff12b78
Source dataset
uspto-grants-2008_07
Patent number
US07396830B2

Reaction notes

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