2-butyl-1,3-diazaspiro[4.4]non-1-en-4-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 19.6 g (0,1 mol) of 1-cyano-1-n-pentanoylaminocyclopentane dissolved in 70 ml of methanol, 5 g of Varion AD resin was added the reaction mixture was heated under reflux conditions for 3 hours. After filtration and evaporation 16.5 g (71.7%) of title compound was obtained, assay by GC: 92%. 5 g of Varion AD resin was added the reaction mixture was heated under reflux conditions for 3 hours After filtration evaporation 16.5 g (71.7%) of title compound was obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 19.6 g (0,1 mol) of 1-cyano-1-n-pentanoylaminocyclopentane dissolved in 70 ml of methanol, 5 g of Varion AD resin was added the reaction mixture was heated under reflux conditions for 3 hours. After filtration and evaporation 16.5 g (71.7%) of title compound was obtained, assay by GC: 92%. 5 g of Varion AD resin was added the reaction mixture was heated under reflux conditions for 3 hours After filtration evaporation 16.5 g (71.7%) of title compound was obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 19.6 g (0,1 mol) of 1-cyano-1-n-pentanoylaminocyclopentane dissolved in 70 ml of methanol, 5 g of Varion AD resin was added the reaction mixture was heated under reflux conditions for 3 hours. After filtration and evaporation 16.5 g (71.7%) of title compound was obtained, assay by GC: 92%. 5 g of Varion AD resin was added the reaction mixture was heated under reflux conditions for 3 hours After filtration evaporation 16.5 g (71.7%) of title compound was obtained

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. the mixture is heated at reflux for 1 hr 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 the resulting solid is filtered

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. the mixture is heated at reflux for 1 hr 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 the resulting solid is filtered

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A RB flask was charged with 2-(n-butyl)-1,3-diazaspiro[4,4]non-1-ene-4-one (7.0 g), toluene (70 ml), DMF (30 ml) and sodium methoxide (2.2 g) at room temperature and stirred for 15 min, followed by the addition of 4-(bromomethyl)-2′-cyanobiphenyl (10 g). The reaction mixture was stirred for 1 hour and then quenched by the addition of water (100 ml). The layers were separated and organic layer was evaporated to get oily residue. The obtained residue was taken in isopropyl alcohol (10 ml) and water (10 ml) and stirred at room temperature to get solid material. The solid material was filtered and washed with IPA and water mixture and then dried under vacuum. The reaction mixture was stirred for 1 hour quenched by the addition of water (100 ml) The layers were separated organic layer was evaporated to get oily residue to get solid material The solid material was filtered washed with IPA and water mixture dried under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A RB flask was charged with 2-(n-butyl)-1,3-diazaspiro[4,4]non-1-ene-4-one (7.0 g), toluene (70 ml), DMF (30 ml) and sodium methoxide (2.2 g) at room temperature and stirred for 15 min, followed by the addition of 4-(bromomethyl)-2′-cyanobiphenyl (10 g). The reaction mixture was stirred for 1 hour and then quenched by the addition of water (100 ml). The layers were separated and organic layer was evaporated to get oily residue. The obtained residue was taken in isopropyl alcohol (10 ml) and water (10 ml) and stirred at room temperature to get solid material. The solid material was filtered and washed with IPA and water mixture and then dried under vacuum. The reaction mixture was stirred for 1 hour quenched by the addition of water (100 ml) The layers were separated organic layer was evaporated to get oily residue to get solid material The solid material was filtered washed with IPA and water mixture dried under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A RB flask was charged with 2-(n-butyl)-1,3-diazaspiro[4,4]non-1-ene-4-one (7.0 g), toluene (70 ml), DMF (30 ml) and sodium methoxide (2.2 g) at room temperature and stirred for 15 min, followed by the addition of 4-(bromomethyl)-2′-cyanobiphenyl (10 g). The reaction mixture was stirred for 1 hour and then quenched by the addition of water (100 ml). The layers were separated and organic layer was evaporated to get oily residue. The obtained residue was taken in isopropyl alcohol (10 ml) and water (10 ml) and stirred at room temperature to get solid material. The solid material was filtered and washed with IPA and water mixture and then dried under vacuum. The reaction mixture was stirred for 1 hour quenched by the addition of water (100 ml) The layers were separated organic layer was evaporated to get oily residue to get solid material The solid material was filtered washed with IPA and water mixture dried under vacuum