Water → HCID 46199062, compound

HRID 1966450Notes

Reaction equation

HRID 1966450 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:16]=[CH:17][C:18]([N+:28]([O-:30])=[O:29])=[C:19]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:20]=2)[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:31]I.[OH-].[Na+].O>CN(C=O)C>[CH3:31][N:21]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:19]1[CH:20]=[C:15]([N:12]2[CH2:11][CH2:10][N:9]([C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:14][CH2:13]2)[CH:16]=[CH:17][C:18]=1[N+:28]([O-:30])=[O:29]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 44814403HCID 44814403, compound

Product 1

HCID 46199062HCID 46199062, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(4-benzoylpiperazin-1-yl)-2-nitro-N-phenylbenzenamine (2.0 g, 5.00 mmol), methyl iodide (0.31 ml, 5.00 mmol) and sodium hydroxide (0.26 g, 6.5 mmol) in 25 ml DMF was stirred at 0° C. for 2 hours. 100 ml water was added to the mixture to quench the run, and the mixture was extracted with ethyl acetate (2×20 ml). The extraction was washed with water (3×30 ml) and dried over anhydrous sodium sulfate. N-methyl-5-(4-benzoylpiperazin-1-yl)-2-nitro-N-phenylbenzenamine (1.8 g, 90%) was obtained after remove of solvents. 1H NMR (500 MHz, CDCl3) δ (ppm) 3.38 (s, 3H), 3.37-3.87 (m, 8H), 6.72 (m, 4H), 6.84 (m, 1H), 7.21 (m, 2H), 7.45 (m, 5H), 8.07 (d, J=9.9 Hz, 1H). 13C NMR (125 MHz, CDCl3): δ (ppm) 40.5, 47.7, 47.9, 111.1, 114.6, 115.3, 119.8, 127.6, 129.1, 129.2, 129.6, 130.7, 135.6, 137.3, 145.4, 148.4, 155.1, 171.0.

Workup

  1. customto quench the run
  2. extractionthe mixture was extracted with ethyl acetate (2×20 ml)
  3. extractionThe extraction
  4. washwas washed with water (3×30 ml)
  5. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-335dbb87c251412ea1838c46060930a5
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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