Zacopride

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

Procedure: To a solution of sodium ethanethiolate in DMF is added 4-amino-N-(1-azabicyclo[2.2.2]oct-3-yl)-5-chloro-2-methoxybenzamide and the mixture heated under reflux to 1 h. After cooling, the mixture is neutralized with hydrochloric acid, concentrated in vacuo and the residue purified by chromatography to give the title compound. the mixture heated under reflux to 1 h After cooling concentrated in vacuo the residue purified by chromatography

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

Procedure: To a solution of sodium ethanethiolate in DMF is added 4-amino-N-(1-azabicyclo[2.2.2]oct-3-yl)-5-chloro-2-methoxybenzamide and the mixture heated under reflux to 1 h. After cooling, the mixture is neutralized with hydrochloric acid, concentrated in vacuo and the residue purified by chromatography to give the title compound. the mixture heated under reflux to 1 h After cooling concentrated in vacuo the residue purified by chromatography

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

Procedure: A solution of 4-amino-N-(1-azabicyclo[2.2.2]oct-3-yl)-5-chloro-2-methoxybenzamide (4.03 g, 13 mmol) in dimethylformamide dimethyl acetal (15 mL) and anhydrous dimethylformamide (5 mL) was heated to 100° C. for 4 hours, then concentrated in vacuo. The residue was dissolved in 6:1 tetrahydrofuran/methanol and filtered through a short column of alumina (eluted with 6:1 tetrahydrofuran/methanol). The filtrate was concentrated in vacuo to a purple residue, which was triturated from cold ether and recrystallized (2 crops) from acetonitrile to afford 2.88 g (61%) of fine colorless needles; mp 178.5°-179.5° C. concentrated in vacuo The residue was dissolved in 6:1 tetrahydrofuran/methanol filtered through a short column of alumina (eluted with 6:1 tetrahydrofuran/methanol) The filtrate was concentrated in vacuo to a purple residue, which was triturated from cold ether recrystallized (2 crops) from acetonitrile

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

Procedure: To a solution of sodium ethanethiolate in DMF is added 4-amino-N-(1-azabicyclo[2.2.2]oct-3-yl)-5-chloro-2-methoxybenzamide and the mixture heated under reflux to 1 h. After cooling, the mixture is neutralized with hydrochloric acid, concentrated in vacuo and the residue purified by chromatography to give the title compound. the mixture heated under reflux to 1 h After cooling concentrated in vacuo the residue purified by chromatography