Potassium Carbonate → Dimethyl-[1-(3-methyl-4-nitrophenyl)pyrrolidin-3-yl]amine

HRID 72194

Reaction equation

HRID 72194 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH3:11])[CH:3]=1.[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>[CH3:12][N:13]([CH3:19])[CH:14]1[CH2:18][CH2:17][N:16]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH3:11])[CH:3]=2)[CH2:15]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 949565-Fluoro-2-nitrotolueneHCID 27585193-(Dimethylamino)pyrrolidine

Product 1

HCID 68977058Dimethyl-[1-(3-methyl-4-nitrophenyl)pyrrolidin-3-yl]amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-fluoro-2-methyl-1-nitrobenzene (13.6 g), dimethylpyrrolidin-3-ylamine (10.0 g), potassium carbonate (12 g) and DMF (100 mL) was stirred at room temperature for 4 hours. The reaction mixture was partitioned between water and ethyl acetate. The organic phase was dried and concentrated. The product with the molecular weight of 249.32 (C13H19N3O2) was obtained in this way; MS (ESI): 250 (M+H+).

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. customThe organic phase was dried
  3. concentrationconcentrated
  4. customThe product with the molecular weight of 249.32 (C13H19N3O2) was obtained in this way

Sources & evidence

ORD record
ord-0875dc4f41854179839123d1593d5957
Source dataset
uspto-grants-2014_09
Patent number
US08828991B2

Linked notes

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