Water → 1-(2-(2-Methoxy-4-nitrophenoxy)ethyl)pyrrolidine

HRID 491213

Reaction equation

HRID 491213 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[O-:12].[K+].Cl.Cl[CH2:16][CH2:17][N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[O:12][CH2:16][CH2:17][N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 14144719HCID 14144719, compound

Product 1

HCID 179893551-(2-(2-Methoxy-4-nitrophenoxy)ethyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of potassium 2-methoxy-4-nitro-phenolate (2.0 g, 9.7 mmol), 1-(2-chloro-ethyl)-pyrrolidine hydrochloride (2.0 g, 12 mmol) and cesium carbonate (7.0, 22 mmol) in DMF (35 mL) was heated at 80° C. for 16 h. The mixture was allowed to cool to room temperature, poured into water (60 mL) and extracted with EtOAc (2×50 mL). The combined extracts were washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated and used in the next step without purification.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with EtOAc (2×50 mL)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customused in the next step without purification

Sources & evidence

ORD record
ord-c3f8596d21e044b3802d5d13715720ab
Source dataset
uspto-grants-2009_05
Patent number
US07528143B2

Linked notes

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