Réaction #46962

Équation de réaction

hydrochloride

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

potassium hydroxide

4-iodobenzyl bromide

→

title compound

Rendement 88.0%

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

Rendement 88.0%

Solvants

water

toluene

water

Conditions de réaction

Traitement

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

Mode opératoire

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