2-Chloro-1-fluoro-4-nitrobenzene → (2-Chloro-4-nitro-phenyl)-methyl(1-methyl-pyrrolidin-3-yl)-amine

HRID 1531176Notes

Reaction equation

HRID 1531176 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[CH3:12][NH:13][CH:14]1[CH2:18][N:17]([CH3:19])[CH2:16][CH2:15]1>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[N:13]([CH3:12])[CH:14]1[CH2:15][CH2:16][N:17]([CH3:19])[CH2:18]1

Participants

4

Reactant 2

HCID 676882-Chloro-1-fluoro-4-nitrobenzeneHCID 2758520N,1-dimethylpyrrolidin-3-amine

Product 1

HCID 18543297(2-Chloro-4-nitro-phenyl)-methyl(1-methyl-pyrrolidin-3-yl)-amine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-Chloro-4-fluoronitrobenzene (1.0 g) and N,N′-dimethyl-3-aminopyrrolidine (1.72 g) are combined and stirred for approximately 24 hours. The mixture is then diluted with ethyl acetate, washed twice with water and once with saturated sodium chloride, and dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure the residue is chromatographed over silica gel (pure ethyl acetate followed by pure methanol is used as the eluants) to provide the desired product as a yellow oil. p Using the above procedure and appropriate starting materials the following compounds were prepared:

Workup

  1. washwashed twice with water and once with saturated sodium chloride
  2. dry with materialdried over anhydrous sodium sulfate
  3. customAfter removal of the solvent under reduced pressure the residue
  4. customis chromatographed over silica gel (pure ethyl acetate

Sources & evidence

ORD record
ord-13e9fd38157a4a72981f019a1fc1de62
Source dataset
uspto-grants-2001_03
Patent number
US06197803B1

Reaction notes

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