ethyl N-piperidin-4-ylcarbamate

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

Procedure: Ethyl 4-piperidylcarbamate (2 g), from Preparation 4, and 5-(2,3-epoxypropoxy)-3,4-dihydrocarbostyril (2.54 g), from Preparation 5, were dissolved in ethanol (50 mL) and the resulting solution was heated under reflux for 6 hours and then cooled to room temperature. Concentrated hydrochloric acid (1 mL) was added. A white product precipitated, which was collected by filtration. The crude product was recrystallized from ethanol to yield 2.8 g (56.5%) of 3,4-dihydro-5-[2-hydroxy-3-(4-(ethoxycarbonylamino)-1-piperidyl)propoxy]carbostyril hydrochloride, m.p. 232°-234° C. (dec.). from Preparation 5 the resulting solution was heated under reflux for 6 hours A white product precipitated which was collected by filtration The crude product was recrystallized from ethanol

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

Procedure: 11 g (64 mmol) of 4-ethoxycarbonylaminopiperidine, 20.5 g (64 mmol) of 4,4-bis(4-fluorophenyl)butyl bromide, 12.9 g (128 mmol) of triethylamine and 0.18 g of potassium iodide were stirred in 180 ml of absolute dimethylformamide at 80° C. for 36 hours, the mixture was diluted with about 1.5 liters of water, 100 ml of 2N NaOH were added and the mixture was extracted twice with methylene chloride. were added the mixture was extracted twice with methylene chloride

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

Procedure: 16 g (61 mmol) of 1-benzyl-4-ethoxycarbonylaminopiperidine were hydrogenated in 240 ml of methanol and 80 ml of 10% strength methanolic hydrochloric acid on 4 g of palladium-on-charcoal (10%) at 45° C. in a shaking vessel for 90 minutes. The catalyst was filtered off with suction, the solvent was evaporated off, the residue was dissolved in 400 ml of ethanol and the solution was neutralized with ethanolic NaOH. The NaCl which had precipitated out was filtered off and the filtrate was concentrated. The catalyst was filtered off with suction the solvent was evaporated off the residue was dissolved in 400 ml of ethanol The NaCl which had precipitated out was filtered off the filtrate was concentrated

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

Procedure: A mixture of commercially available ethyl piperidin-4-ylcarbamate (2.067 g, 12 mmol) and isobutylene oxide (868 mg, 12 mmol) in ethanol (15 mL) was irradiated in a microwave apparatus at 110° C. for 90 min. Purification by silica gel column chromatography with ethyl acetate gave the title compound as a colorless oil (2.838 g, 97%); MS: m/e=245.3 (M+H+). was irradiated in a microwave apparatus at 110° C. for 90 min Purification by silica gel column chromatography with ethyl acetate

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

Procedure: Ethyl 4-piperidylcarbamate (2 g), from Preparation 4, and 5-(2,3-epoxypropoxy)-3,4-dihydrocarbostyril (2.54 g), from Preparation 5, were dissolved in ethanol (50 mL) and the resulting solution was heated under reflux for 6 hours and then cooled to room temperature. Concentrated hydrochloric acid (1 mL) was added. A white product precipitated, which was collected by filtration. The crude product was recrystallized from ethanol to yield 2.8 g (56.5%) of 3,4-dihydro-5-[2-hydroxy-3-(4-(ethoxycarbonylamino)-1-piperidyl)propoxy]carbostyril hydrochloride, m.p. 232°-234° C. (dec.). from Preparation 5 the resulting solution was heated under reflux for 6 hours A white product precipitated which was collected by filtration The crude product was recrystallized from ethanol