Formaldehyde → 1-[4-(pyrrolidinyl)-2-butynyl]-1H-imidazole
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]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- customThe solvent was evaporated
- dissolutionthe residual oil was dissolved in chloroform
- filtrationfiltered
- 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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