Water → Ethyl 4-(3-(4-acetyl-1-piperazinyl)-phenyl)-amino-6-fluoro-3-nitrobenzoate

HRID 480002

Reaction equation

HRID 480002 reaction equation
[F:1][C:2]1[CH:12]=[C:11](F)[C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:17]([N:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:27]=[C:28]([CH:30]=[CH:31][CH:32]=2)N)[CH2:22][CH2:21]1)(=[O:19])[CH3:18].C([N:35](CC)CC)C.O>CN1C(=O)CCC1>[C:17]([N:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:27]=[C:28]([C:11]3[CH:12]=[C:2]([F:1])[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:9]([NH2:35])[C:10]=3[N+:14]([O-:16])=[O:15])[CH:30]=[CH:31][CH:32]=2)[CH2:22][CH2:21]1)(=[O:19])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 111175391-[4-(3-Aminophenyl)piperazin-1-yl]ethan-1-oneHCID 22330120Ethyl 2,4-difluoro-5-nitrobenzoate

Product 1

HCID 86592319Ethyl 4-(3-(4-acetyl-1-piperazinyl)-phenyl)-amino-6-fluoro-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 2,4difluoro-5-nitrobenzoate (22) (1.0 g; 4.33 mmol), 4f (0.95 g; 4.33 mmol) and triethylamine (0.6 ml; 0.33 mmol) in anhydrous NMP (10 ml) was heated to 80° C. for one hour. The cooled mixture was poured into water and extracted with ethyl acetate. The organic extract was dried over magnesium sulphate, concentrated under reduced pressure and purified by column-chromatography on silica gel using ethyl acetate as the eluent. Yield: 1.53 g (82%).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. dry with materialwas dried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. custompurified by column-chromatography on silica gel

Sources & evidence

ORD record
ord-f60e53fbf16d4216930254366e7b9374
Source dataset
uspto-grants-2003_11
Patent number
US06649609B2

Linked notes

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