Potassium Carbonate → (1-Benzyl-4-methyl-piperidin-4-yl)-(2-nitro-phenyl)-amine

HRID 239116Notes

Reaction equation

HRID 239116 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].C(=O)([O-])[O-].[K+].[K+].[CH2:17]([N:24]1[CH2:29][CH2:28][C:27]([NH2:31])([CH3:30])[CH2:26][CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CS(C)=O.O>[CH2:17]([N:24]1[CH2:29][CH2:28][C:27]([NH:31][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])([CH3:30])[CH2:26][CH2:25]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 221467251-Benzyl-4-methylpiperidin-4-amine

Product 1

HCID 86686491(1-Benzyl-4-methyl-piperidin-4-yl)-(2-nitro-phenyl)-amineYield 71.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

3.6 g 1-fluor-2-nitrobenzene and 82.7 g potassiumcarbonate were added to 5.3 g 1-benzyl-4-methyl-piperidin-4-ylamine in 50 mL DMSO and the mixture was stirred at 150° C. 24 h. The reaction was diluted with water and the aqueous layer was extracted with ethylacetate. The organic layer was evaporated and the residue purified by column chromatographie on silica gel (heptane/ethylacetate:9/1) to give 5.9 g of the desired product.

Workup

  1. custom24 h
  2. extractionthe aqueous layer was extracted with ethylacetate
  3. customThe organic layer was evaporated
  4. customthe residue purified by column chromatographie on silica gel (heptane/ethylacetate:9/1)

Sources & evidence

ORD record
ord-db6d0720f78140feb2ec82487db2a165
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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