ethyl 2-piperidin-3-ylacetate

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 a mixture of 2-bromomethyl-2,3-dihydrobenzo[1,4]dioxine (1.34 g, 5.84 mmol), piperidin-3-yl-acetic acid ethyl ester (1.0 g, 5.84 mmol) in acetonitrile (25 ml) was added K2CO3 (0.81 g, 5.84 mmol) and KI (0.97 g, 5.84 mmol). The reaction mixture was irradiated under microwaves at 82° C. for 8 h. Water (100 ml) was then added. The reaction mixture was extracted with DCM (3×50 ml). The combined organic phases were dried (Na2SO4), filtered and the filtrate was evaporated to give the title compound, which was purified by column chromatography (DCM/MeOH, 95:5). The reaction mixture was irradiated under microwaves at 82° C. for 8 h The reaction mixture was extracted with DCM (3×50 ml) The combined organic phases were dried (Na2SO4) filtered the filtrate was evaporated

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

Procedure: To a mixture of 2-bromomethyl-2,3-dihydrobenzo[1,4]dioxine (1.34 g, 5.84 mmol), piperidin-3-yl-acetic acid ethyl ester (1.0 g, 5.84 mmol) in acetonitrile (25 ml) was added K2CO3 (0.81 g, 5.84 mmol) and KI (0.97 g, 5.84 mmol). The reaction mixture was irradiated under microwaves at 82° C. for 8 h. Water (100 ml) was then added. The reaction mixture was extracted with DCM (3×50 ml). The combined organic phases were dried (Na2SO4), filtered and the filtrate was evaporated to give the title compound, which was purified by column chromatography (DCM/MeOH, 95:5). The reaction mixture was irradiated under microwaves at 82° C. for 8 h The reaction mixture was extracted with DCM (3×50 ml) The combined organic phases were dried (Na2SO4) filtered the filtrate was evaporated

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

Procedure: This reaction was run in the same manner as ethyl 3-piperidinylacetate, starting with commercially available N,N-dimethylnicotinamide (10 g; 66.7 mmol) and platinum oxide (1.02 g; 4.49 mmol). Trifluoroacetic acid (5.1 ml; 66.2 mmol) was used in place of L(+) tartaric acid. Crude product was purified by distillation at approximately 150° C./10 torr, giving N,N-dimethyl-3-piperidinecarboxamide (4.0 g) as a colorless oil. MS m/z (positive ion) 157 (MH+: 100). Crude product was purified by distillation at approximately 150° C./10 torr

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

Procedure: The reaction was run in the same manner as ethyl 1-benzoyl-3-piperidinecarboxylate, starting with ethyl 3-piperidinylacetate (414.2 mg; 2.4 mmol) and 2-thiopheneacetyl chloride (295 μl; 2.4 mmol). The crude product was purified by chromatography on silica, eluting with 50% ethyl acetate in hexane, giving ethyl 1-(2-thiopheneacetyl)-3-piperidinylacetate (364 mg) as a pale yellow oil. MS m/z (positive ion) 318 (M+Na+; 40), 296 (MH+; 100). The crude product was purified by chromatography on silica eluting with 50% ethyl acetate in hexane

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

Procedure: The reaction was run in the same manner as ethyl 3-piperidinylacetate, starting with commercially available ethyl-2-pyridylacetate (4.00 g; 24.5 mmol). This gave ethyl 2-piperidinylacetate (2.41 g) as a light yellow oil without further purification. MS m/z (positive ion) 172 (MH+; 100). This gave ethyl 2-piperidinylacetate (2.41 g) as a light yellow oil without further purification

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

Procedure: Commercially available ethyl-3-pyridylacetate (4.04 g; 24.5 mmol) was dissolved in absolute ethanol (100 ml). L(+) tartaric acid (3.67 g; 24.5 mmol) and platinum oxide (546.1 mg; 2.4 mmol) were added, and the partial suspension was placed under hydrogen gas at 50 psi with shaking for 24 hours. The hydrogen was removed, and the mixture was then filtered through celite to remove the catalyst. The filtrate was evaporated at ambient temperature under reduced pressure to a small volume. This residue was diluted with saturated sodium bicarbonate solution and extracted with ethyl acetate. The aqueous solution was then basified with 1 N sodium hydroxide and extracted with fresh ethyl acetate. The ethyl acetate extracts were combined, dried with anhydrous potassium carbonate, and evaporated at ambient temperature under reduced pressure, giving ethyl 3-piperidinylacetate (2.96 g) as a very pale yellow oil without further purification. MS m/z (positive ion) 172 (MH+; 100). The hydrogen was removed the mixture was then filtered through celite to remove the catalyst The filtrate was evaporated at ambient temperature under reduced pressure to a small volume This residue was diluted with saturated sodium bicarbonate solution extracted with ethyl acetate extracted with fresh ethyl acetate dried with anhydrous potassium carbonate evaporated at ambient temperature under reduced pressure

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 a mixture of 2-bromomethyl-2,3-dihydrobenzo[1,4]dioxine (1.34 g, 5.84 mmol), piperidin-3-yl-acetic acid ethyl ester (1.0 g, 5.84 mmol) in acetonitrile (25 ml) was added K2CO3 (0.81 g, 5.84 mmol) and KI (0.97 g, 5.84 mmol). The reaction mixture was irradiated under microwaves at 82° C. for 8 h. Water (100 ml) was then added. The reaction mixture was extracted with DCM (3×50 ml). The combined organic phases were dried (Na2SO4), filtered and the filtrate was evaporated to give the title compound, which was purified by column chromatography (DCM/MeOH, 95:5). The reaction mixture was irradiated under microwaves at 82° C. for 8 h The reaction mixture was extracted with DCM (3×50 ml) The combined organic phases were dried (Na2SO4) filtered the filtrate was evaporated

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

Procedure: To a mixture of 2-bromomethyl-2,3-dihydrobenzo[1,4]dioxine (1.34 g, 5.84 mmol), piperidin-3-yl-acetic acid ethyl ester (1.0 g, 5.84 mmol) in acetonitrile (25 ml) was added K2CO3 (0.81 g, 5.84 mmol) and KI (0.97 g, 5.84 mmol). The reaction mixture was irradiated under microwaves at 82° C. for 8 h. Water (100 ml) was then added. The reaction mixture was extracted with DCM (3×50 ml). The combined organic phases were dried (Na2SO4), filtered and the filtrate was evaporated to give the title compound, which was purified by column chromatography (DCM/MeOH, 95:5). The reaction mixture was irradiated under microwaves at 82° C. for 8 h The reaction mixture was extracted with DCM (3×50 ml) The combined organic phases were dried (Na2SO4) filtered the filtrate was evaporated