Potassium Carbonate → 1-(2-Nitrophenyl)pyrrolidine

HRID 1816275Notes

Reaction equation

HRID 1816275 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 124141441-(2-Nitrophenyl)pyrrolidineYield 13%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

|2-Fluoronitrobenzene (2.82 g, 20 mmol) was mixed with pyrrolidine (1.56 g, 22 mmol), and potassium carbonate (5.5 g, 40 mmol) in DMF (10 mL). After beating for 16 hours, the mixture was filtered and the filtrate evaporated in vacuo to an oil. This oil was treated with water (10 mL) and dichloromethane (100 mL). The organic phase was collected, dried (MgSO4), filtered, and evaporated to give 1-(2-nitrophenyl)pyrrolidine (0.5 g). The crude product was reduced using 5% palladium on carbon (0.1 g) in ethanol (30mL) and hydrogen at 40 psi for 2 hours. The solution was filtered through celite to remove catalyst and the filtrate evaporated in vacuo to give 2-(1-pyrrolidino)aniline (0.33 g). The crude product was coupled with CMI, under conditions described in the general procedure for CM couplings, to give N-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2-(1-pyrrolidinyl)aniline.

Workup

  1. filtrationthe mixture was filtered
  2. customthe filtrate evaporated in vacuo to an oil
  3. additionThis oil was treated with water (10 mL) and dichloromethane (100 mL)
  4. customThe organic phase was collected
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-94977385d8a342d7b4a046cc77ff3165
Source dataset
uspto-grants-2005_04
Patent number
US06884801B1

Reaction notes

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