Pyrrolidine → 1-[2-(3-Methoxy-4-nitrophenyl)ethyl]pyrrolidine

HRID 871890Notes

Reaction equation

HRID 871890 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]=[CH2:10])[CH:6]=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1>CO>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:6]=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 536287222-Methoxy-1-nitro-4-vinylbenzene

Product 1

HCID 673259461-[2-(3-Methoxy-4-nitrophenyl)ethyl]pyrrolidineYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

3.07 g (17.17 mmol) of the product prepared in step 24.1 and 7.13 mL (85.84 mL) of pyrrolidine in 60 mL of anhydrous methanol are placed in a sealed tube. The mixture is heated under pressure at 100°C. for 4 hours. After cooling to room temperature, it is evaporated to dryness. The residue obtained is purified by chromatography on a column of silica, eluting with a dichloromethane/methanol gradient (100/0 to 90/10). 3.22 g of the expected product are obtained in the form of a yellow solid. Yield=75%.

Workup

  1. temperatureAfter cooling to room temperature
  2. customit is evaporated to dryness
  3. customThe residue obtained
  4. customis purified by chromatography on a column of silica
  5. washeluting with a dichloromethane/methanol gradient (100/0 to 90/10)

Sources & evidence

ORD record
ord-b84e8ff85c2e4944b67dca9bd835a855
Source dataset
uspto-grants-2015_03
Patent number
US08975250B2

Reaction notes

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