p-Fluoronitrobenzene → HCID 68697309, compound

HRID 2236711Notes

Reaction equation

HRID 2236711 reaction equation
[OH-].[K+].[CH3:3][NH:4][CH:5]1[CH2:9][N:8]([CH3:10])[CH2:7][CH2:6]1.F[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1>CS(C)=O>[CH3:3][N:4]([CH:5]1[CH2:6][CH2:7][N:8]([CH3:10])[CH2:9]1)[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 14797Potassium HydroxideHCID 2758520N,1-dimethylpyrrolidin-3-amine

Product 1

HCID 68697309HCID 68697309, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
62.5 °C

Procedure

To a suspension of potassium hydroxide (1.4 g, 25 mmol) and N,N′-dimethyl-3-aminopyrrolidine (1.4 g, 12 mmol) in dimethylsulfoxide (13 mL) is added dropwise 4-fluoronitrobenzene (1.1 mL, 10 mmol). The mixture is heated in a 60-65° C. oil bath for 4 hours. After cooling to room temperature, ice is added to the reaction mixture. The resulting precipitate is collected, washed with water, and dried under vacuum to give methyl-(1-methyl-pyrrolidin-3-yl)-(4-nitro-phenyl)-amine.

Workup

  1. temperatureAfter cooling to room temperature
  2. additionice is added to the reaction mixture
  3. customThe resulting precipitate is collected
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-436f47049e724f13917d5abf3be6df5b
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…