Reaction #46962

Reaction equation

hydrochloride

2-butyl-1,3-diazaspiro[4,4]non-1-en-4-one

potassium hydroxide

4-iodobenzyl bromide

→

title compound

Yield 88.0%

2-butyl-3-(4′-iodobenzyl)-1,3-diazaspiro[4,4]non-1-en-4-one

Yield 88.0%

Solvents

water

toluene

water

Conditions

Workup

1. 1
   Temperaturethe mixture is heated
2. 2
   Temperatureat reflux for 1 hr
3. 3
   Otherthe phases are separated
4. 4
   workup.ADDITIONTo the organic phase is added 10 mL of concentrated hydrochloric acid, 100 mL
5. 5
   Otheris evaporated at reduced pressure, 300 mL of ethyl acetate
6. 6
   workup.ADDITIONis added
7. 7
   Filtrationthe resulting solid is filtered

Procedure

A solution of 23.07 g (100 mmol) of the hydrochloride of 2-butyl-1,3-diazaspiro[4,4]non-1-en-4-one and 19.8 g of potassium hydroxide in 100 mL de water is added to a solution of 29.7 g (100 mmol) of 4-iodobenzyl bromide and 3.4 g (10 mmol) of tetrabutylammonium bisulphate in 30 mL of toluene, and the mixture is heated at reflux for 1 hr. After cooling to 25° C., 100 mL of water is added and the phases are separated. To the organic phase is added 10 mL of concentrated hydrochloric acid, 100 mL is evaporated at reduced pressure, 300 mL of ethyl acetate is added and the resulting solid is filtered to give 39.6 g (88%) of the title compound in the form of hydrochloride.

Source