piperidine-2-carboxamide

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

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

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: An amount of 19.2 g. (0.15 moles) of pipecolamide is added portionwise to 102 g. (1.0 moles) of acetic anhydride over a 15 minute period with stirring. The temperature rises to ca. 60°C. The mixture is then heated to reflux, during which the solid dissolves and the solution turns a dark brown. After refluxing for 4 hours, the reaction mixture is subjected to vacuum distillation (first at 60 mm Hg to remove acetic acid and excess acetic anhydride, and then at 1-4 mm Hg pressure). Thus is obtained 15.3 grams of 1-acetyl-2-cyanopiperidine, boiling at 104°-14°C. This corresponds to a 67% yield based on pipecolamide. rises to ca. 60°C The mixture is then heated to reflux, during which the solid dissolves After refluxing for 4 hours the reaction mixture is subjected to vacuum distillation (first at 60 mm Hg to remove acetic acid and excess acetic anhydride

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

Procedure: The title compound was synthesized in analogy to Example 47 b, using 5-cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid (Example 3 c, 100 mg, 429 μmol) and 2-piperidinecarboxamide (CAN 19889-77-1, 60.4 mg, 472 μmol) as starting materials and isolated (135 mg, 92%) as white solid; LC-MS (UV peak area, ESI) 100%, 344.1972 [MH+]. isolated (135 mg, 92%) as white solid

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

Procedure: The title compound was synthesized in analogy to Example 47 b, using 5-cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid (Example 3 c, 100 mg, 429 μmol) and 2-piperidinecarboxamide (CAN 19889-77-1, 60.4 mg, 472 μmol) as starting materials and isolated (135 mg, 92%) as white solid; LC-MS (UV peak area, ESI) 100%, 344.1972 [MH+]. isolated (135 mg, 92%) as white solid

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

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

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: N-benzyloxypiperidine-2-carboxylic acid (2.0 g), 1-hydroxybenzotriazole (1.6 g), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.3 g) were dissolved in methylene chloride (20 mL). Concentrated aqueous ammonia (3 mL) and triethylamine (2 mL) were added to the resultant solution at room temperature, followed by stirring for 3 days. The reaction mixture was partitioned between water and methylene chloride. The organic layer was dried over magnesium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure. 10% Palladium-carbon (1 g, 50% wet) was added to the residue in methanol (30 mL), and the resultant mixture was stirred in a hydrogen atmosphere for 20 hours. The catalyst was removed by filtration. The solvent was evaporated under reduced pressure, and the thus-obtained oily product was dried, to thereby give the title compound as a solid (970 mg, quantitative amount). The reaction mixture was partitioned between water and methylene chloride The organic layer was dried over magnesium sulfate anhydrate followed by filtration The solvent was evaporated under reduced pressure 10% Palladium-carbon (1 g, 50% wet) was added to the residue in methanol (30 mL) the resultant mixture was stirred in a hydrogen atmosphere for 20 hours The catalyst was removed by filtration The solvent was evaporated under reduced pressure the thus-obtained oily product was dried