Potassium Carbonate → [1-(2-Chloro-4-nitrophenyl)pyrrolidin-3-yl]dimethylamine

HRID 69407

Reaction equation

HRID 69407 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1F.[CH3:12][N:13]([CH3:19])[CH:14]1[CH2:18][CH2:17][NH:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:16]1[CH2:17][CH2:18][CH:14]([N:13]([CH3:19])[CH3:12])[CH2:15]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 676882-Chloro-1-fluoro-4-nitrobenzeneHCID 27585193-(Dimethylamino)pyrrolidine

Product 1

HCID 53440459[1-(2-Chloro-4-nitrophenyl)pyrrolidin-3-yl]dimethylamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-chloro-1-fluoro-4-nitrobenzene (4.79 g), dimethylpyrrolidin-3-ylamine (2.60 g), potassium carbonate (3.82 g) and DMF (35 mL) was stirred at room temperature for 4 hours. The reaction mixture was partitioned between water and ethyl acetate. The organic phase was extracted with hydrochloric acid (2 M), and the extract was basified with sodium hydroxide solution (2M). Extraction with ethyl acetate afforded an organic phase which was dried and concentrated. The product with the molecular weight of 269.73 (C12H16ClN3O2) was obtained in this way; MS (ESI): 270 (M+H+).

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. extractionThe organic phase was extracted with hydrochloric acid (2 M)
  3. extractionExtraction with ethyl acetate
  4. customafforded an organic phase which
  5. customwas dried
  6. concentrationconcentrated
  7. customThe product with the molecular weight of 269.73 (C12H16ClN3O2) was obtained in this way

Sources & evidence

ORD record
ord-bfb5cb4e6bee41f1981849247ce6bbfc
Source dataset
uspto-grants-2014_09
Patent number
US08822495B2

Linked notes

Loading…