Reaction #2200610

Reaction equation

N-(chloroacetyl)pyrrolidine

1,2-dimethylimidazole

acetonitrile

→

white solid

Yield 41.0%

3-[2-(1-pyrrolidinyl)-2-oxoethyl]-1,2-dimethylimidazolium chloride

Yield 41.0%

Solvents

Tert-butyl methylether

Conditions

Workup

1. 1
   Temperatureheating
2. 2
   workup.WAITto stand at room temperature overnight
3. 3
   FiltrationThe product was recovered by filtration
4. 4
   Washwashed with a mixture of tert-butyl methyl ether and acetonitrile (7:3 v/v, 50 mL)
5. 5
   OtherThe crude product was recrystallized from a mixture of acetonitrile and tert-butyl methyl ether

Procedure

A mixture of N-(chloroacetyl)pyrrolidine (2.0 g, 13.55 mmol) and 1,2-dimethylimidazole (1.3 g, 13.5 mmol) were heated neat at 110° C. for 3 hours. To the reaction mixture was added acetonitrile (5 mL), and heating was continued for 20 minutes. Tert-butyl methylether (10 mL) was added, and the resulting mixture was allowed to stand at room temperature overnight. The product was recovered by filtration, and washed with a mixture of tert-butyl methyl ether and acetonitrile (7:3 v/v, 50 mL). The crude product was recrystallized from a mixture of acetonitrile and tert-butyl methyl ether to obtain 1.23 g (41%) of a white solid; mp 191-193° C.

Source