1-Pyrrolidineethanamine → HCID 58016021, compound

HRID 2189269Notes

Reaction equation

HRID 2189269 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1.[NH2:11][CH2:12][CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[N+:8]([C:4]1[CH:3]=[C:2]([NH:11][CH2:12][CH2:13][N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:7]=[CH:6][CH:5]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 13441-PyrrolidineethanamineHCID 98231-Fluoro-3-nitrobenzeneHCID 10796Cesium carbonate

Product 1

HCID 58016021HCID 58016021, compoundYield 18.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

The mixture of 1-fluoro-3-nitrobenzene (420 mg, 3 mmol) in DMF (1.5 mL), N-(2-aminoethyl)-pyrrolidine (514 mg, 4.5 mmol) and Cs2CO3 (977 mg, 3 mmol) is heated at 100° C. under microwave radiation for 2.5 hours, then concentrated. The mixture is diluted with EtOAc, washed with saturated NaHCO3 aqueous solution and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product is purified by column chromatography (SiO2, MeOH:CH2Cl2=1:99 to 10:90) to give 130 mg of the title compound as a light brown oil.

Workup

  1. concentrationconcentrated
  2. additionThe mixture is diluted with EtOAc
  3. washwashed with saturated NaHCO3 aqueous solution and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product is purified by column chromatography (SiO2, MeOH:CH2Cl2=1:99 to 10:90)

Sources & evidence

ORD record
ord-7348717a1d704ea9bc82a06b9c883250
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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