Cesium carbonate → HCID 66863894, compound

HRID 1985638Notes

Reaction equation

HRID 1985638 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=1.[N:12]1([C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]([F:29])([F:28])[F:27])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[NH2:8][C:6]1[CH:7]=[C:2]([N:15]2[CH2:14][CH2:13][N:12]([C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([F:28])([F:27])[F:29])=[O:19])[CH2:17][CH2:16]2)[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 742185-Chloro-2-nitroanilineHCID 167337841-[2-(Trifluoromethyl)benzoyl]piperazine

Product 1

HCID 66863894HCID 66863894, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 5-chloro-2-nitrophenylamine (3.000 g, 17.38 mmol), piperazin-1-yl-(2-trifluoromethylphenyl)methanone (5.360 g, 20.80 mmol) and cesium carbonate (11.32 g, 34.76 mmol) was heated at 140° C. in anhydrous DMSO (15 mL) for 12 h. The mixture was cooled and poured over ice water. The solid product obtained was extracted with ethyl acetate. The organic extracts were combined, dried over anhydrous sodium sulphate, concentrated in vacuo. The residue was purified by column chromatography to obtain the product, [4-(3-amino-4-nitrophenyl)piperazin-1-yl]-(2-trifluoromethylphenyl)methanone, in 79% yield (6.800 g). 1H NMR (300 MHz, CDCl3) δ 8.01 (d, 1H, J=9.6 Hz), 7.72 (d, 1H, J=7.9 Hz), 7.62 (t, 1H, J=7.1 Hz), 7.54 (t, 1H, J=7.4 Hz), 7.34 (d, 1H, J=7.3 Hz), 6.22 (dd, 1H, J=2.6,9.7 Hz), 6.15 (br. s, 2H), 5.94 (d, 1H, J=2.6 Hz), 4.05-3.93 (m, 1H), 3.90-3.80 (m, 1H), 3.50-3.40 (m, 2H), 3.35-3.20 (m, 4H). MS (ES+) m/z 395.1 (M+1).

Workup

  1. temperatureThe mixture was cooled
  2. customThe solid product obtained
  3. extractionwas extracted with ethyl acetate
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-6c68cdf8fca24d099d06dfb9905dc432
Source dataset
uspto-grants-2009_06
Patent number
US07547698B2

Reaction notes

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