Formaldehyde → 1-[4-(pyrrolidinyl)-2-butynyl]-1H-imidazole

HRID 2372806Notes

Reaction equation

HRID 2372806 reaction equation
[CH2:1]([N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1)[C:2]#[CH:3].[NH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1.[CH2:14]=O>O1CCOCC1>[N:9]1([CH2:14][C:3]#[C:2][CH2:1][N:4]2[CH:8]=[CH:7][N:6]=[CH:5]2)[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 31268PyrrolidineHCID 125919421-(prop-2-yn-1-yl)-1H-imidazole

Product 1

HCID 199022971-[4-(pyrrolidinyl)-2-butynyl]-1H-imidazoleYield 68.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1-(2-propynyl)-1H-imidazole (2.5 g, 0.023 mol), pyrrolidine (2.0 g, 0.026 mol), paraformaldehyde (0.85 , 0.028 mol) and cuprous chloride (30 mg) in dioxane (20 mL) was heated at 50° C. for 4 h. The solvent was evaporated and the residual oil was dissolved in chloroform, filtered, and chromatographed on silica gel to give 2.99 g of 1-[4-(pyrrolidinyl)-2-butynyl]-1H-imidazole as an oil.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residual oil was dissolved in chloroform
  3. filtrationfiltered
  4. customchromatographed on silica gel

Sources & evidence

ORD record
ord-5b00f6120d124f158a1e97087a11de3f
Source dataset
uspto-grants-1992_03
Patent number
US05100909

Reaction notes

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