Pyrrolidine → 1-[(4-ethenylphenyl)methyl]-pyrrolidine

HRID 434146Notes

Reaction equation

HRID 434146 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1)=[CH2:2].[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1>CCCCCC>[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:5][CH:4]=1)=[CH2:2]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 74126p-Vinylbenzyl chloride

Product 1

HCID 120951841-[(4-ethenylphenyl)methyl]-pyrrolidine

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A 1 L (liter) round bottom flask was charged with hexane (400 mL) and 4-vinylbenzyl chloride (104.4 g, 0.68 moles). The reaction flask was placed into an ice/water bath and stirred with a magnetic stir bar. Two equivalents of pyrrolidine (130 g, 1.37 moles) were added over the course of 1 hour. After completed addition the ice/water bath was removed and the reaction was stirred at room, temperature overnight. Solids were removed via vacuum filtration and volatiles were removed under vacuum to render the product in quantitative yield.

Workup

  1. customThe reaction flask was placed into an ice/water bath
  2. customwas removed
  3. stirringthe reaction was stirred at room, temperature overnight
  4. customSolids were removed via vacuum filtration and volatiles
  5. customwere removed under vacuum

Sources & evidence

ORD record
ord-a7ab960968da46a086f2dba605b0d53c
Source dataset
uspto-grants-2003_12
Patent number
US06670471B1

Reaction notes

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