4-(2,6-dimethylpiperidin-1-yl)butan-1-ol

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

Procedure: The procedure is as in Example 7, but starting with 4-(2,6-dimethyl-1-piperidyl)butanol (8 g) in anhydrous tetrahydrofuran (220 cc), an oily suspension (50% by weight; 1.9 g) of sodium hydride and 3-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone (8.6 g). The residue obtained is taken up with ethyl acetate (20 cc); the insoluble product is removed by filtration and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. The residue obtained is taken up with water (50 cc) and 4N aqueous hydrochloric acid solution (20 cc); the remaining insoluble product is removed by filtration. The filtrate is neutralized with 4 N aqueous sodium hydroxide solution and then extracted with methylene chloride (3×100 cc); the organic extracts are combined and washed with water, dried and concentrated to dryness under reduced pressure (3 kPa) at 40° C. The residue obtained is recrystallized successively in ethyl acetate and 2-propanol, and 2-(7-chloro-1,8-naphthyridin-2-yl)-3-[4-(2,6-dimethylpiperidino)butoxy]-1isoindolinone hydrochloride (1.6 g) is thereby obtained. The residue obtained the insoluble product is removed by filtration the filtrate is concentrated to dryness under reduced pressure (2.7 kPa) at 40° C The residue obtained the remaining insoluble product is removed by filtration extracted with methylene chloride (3×100 cc) washed with water dried concentrated to dryness under reduced pressure (3 kPa) at 40° C The residue obtained is recrystallized successively in ethyl acetate