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

HRID 1169006Notes

Reaction equation

HRID 1169006 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-b8ba6b7a048046d184cd40d19e4070e4
Source dataset
uspto-grants-2003_09
Patent number
US06627722B2

Reaction notes

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