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

HRID 1533191Notes

Reaction equation

HRID 1533191 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.

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-265a29e4b7134df7b2aa48ce8164efff
Source dataset
uspto-grants-2001_03
Patent number
US06207715B1

Reaction notes

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