Pyrrolidine → 1-(4-Bromobenzyl)pyrrolidine

HRID 1387017Notes

Reaction equation

HRID 1387017 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11]Br)=[CH:9][CH:8]=1>C(Cl)Cl.CCOC(C)=O>[Br:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 31268PyrrolidineHCID 685274-Bromobenzyl bromide

Product 1

HCID 127380041-(4-Bromobenzyl)pyrrolidineYield 94%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pyrrolidine (20.0 mL, 0.240 mole) was added to a stirred solution of 4-bromobenzyl bromide (10.0 g, 40.0 mmol) in anhydrous CH2Cl2 (20 mL) at 0° C. under nitrogen. The resultant solution was allowed to stir at room temperature for 1 h. The reaction mixture was diluted with EtOAc (150 mL) before it was washed with half-saturated aqueous NaHCO3 (50 mL). After drying over MgSO4, filtration, and concentration, the oily residue was chromatographed on silica [20% EtOAc in hexanes, then 10% EtOH/Et3N (2/1) in THF/hexanes (1/1)] to provide 9.02 g of the benzyl pyrrolidine (94%) as an oil.

Workup

  1. washwas washed with half-saturated aqueous NaHCO3 (50 mL)
  2. dry with materialAfter drying over MgSO4, filtration, and concentration
  3. customthe oily residue was chromatographed on silica [20% EtOAc in hexanes

Sources & evidence

ORD record
ord-6b4c5f1dd995414b9a36e7cfa2201a4a
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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