Ethyl Acetate → (2-Chloro-4-nitro-phenyl)-methyl(1-methyl-pyrrolidin-3-yl)-amine

HRID 990838Notes

Reaction equation

HRID 990838 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.C[N:13]([CH:15]1[CH2:19][NH:18][CH2:17][CH2:16]1)[CH3:14].[C:20](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]([CH3:14])[CH:15]1[CH2:16][CH2:17][N:18]([CH3:20])[CH2:19]1

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 676882-Chloro-1-fluoro-4-nitrobenzeneHCID 27585193-(Dimethylamino)pyrrolidine

Product 1

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

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-8845f66ca33c4084a63887839ae51ddf
Source dataset
uspto-grants-2002_10
Patent number
US06462055B2

Reaction notes

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