Pyrrolidine → 1-[(3-Iodophenyl)methyl]pyrrolidine

HRID 1854598Notes

Reaction equation

HRID 1854598 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Cl.[NH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1>O1CCOCC1>[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][N:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 130599781-(Chloromethyl)-3-iodobenzene

Product 1

HCID 185258711-[(3-Iodophenyl)methyl]pyrrolidineYield 97%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-iodobenzyl chloride (100 mg, 0.396 mmol) in 1,4-dioxane (3 ml) was treated with pyrrolidine (0.5 ml, 6.02 mmol) and heated to reflux for 5 h. The cooled mixture was evaporated to dryness and treated with EtOAc and water. The organics were separated, dried over MgSO4, filtered and evaporated to afford 1-(3-iodo-benzyl)-pyrrolidine as a clear syrup (110 mg, 97%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 5 h
  3. customThe cooled mixture was evaporated to dryness
  4. additiontreated with EtOAc and water
  5. customThe organics were separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-7366a454006d44a69451421d2af28eda
Source dataset
uspto-grants-2015_02
Patent number
US08962665B2

Reaction notes

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