1-benzyl-N-methylpiperidine-4-carboxamide

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 1-benzyl-piperidine-4-carboxylic acid methylamide (36) (853 mg, 3.67 mmol) in dichloromethane (10 ml) was cooled in an ice-bath and phosphorous pentachloride (841 mg, 4 mmol) was added dropwise. The mixture was stirred at rt for 5 h, cooled to −5° C. and trimethylsilyl azide (387 ul, 3.67 mmol) was added dropwise. The reaction mixture was stirred for 3 h at rt and was then quenched by addition of sat. aqueous NaHCO3 solution. The organic layer was washed with water and brine, dried over Na2 SO4 and evaporated to yield a colorless solid. cooled to −5° C. The reaction mixture was stirred for 3 h at rt was then quenched by addition of sat. aqueous NaHCO3 solution The organic layer was washed with water and brine dried over Na2 SO4 evaporated to yield a colorless solid

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 1-benzylpiperidine-4-carboxylic acid (1 g, 4.56 mmol), methylamine (9.12 ml of a 2N solution in THF, 18.2 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (1.75 g, 9.1 mmol) and 1-hydroxybenzotriazole (0.7 g, 4.56 mmol) in 10 ml DMF was stirred at rt for 3 h. The reaction mixture was poured on saturated aqueous NaHCO3 and extracted with ethyl acetate. The organic layer was washed with NaHCO3 solution and brine, dried (Na2 SO4) and evaporated. Drying in vacuo gave a colorless solid which was used in the next step without further purification. extracted with ethyl acetate The organic layer was washed with NaHCO3 solution and brine dried (Na2 SO4) evaporated Drying in vacuo gave a colorless solid which was used in the next step without further purification

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 1-benzyl-piperidine-4-carboxylic acid methylamide (36) (853 mg, 3.67 mmol) in dichloromethane (10 ml) was cooled in an ice-bath and phosphorous pentachloride (841 mg, 4 mmol) was added dropwise. The mixture was stirred at rt for 5 h, cooled to −5° C. and trimethylsilyl azide (387 ul, 3.67 mmol) was added dropwise. The reaction mixture was stirred for 3 h at rt and was then quenched by addition of sat. aqueous NaHCO3 solution. The organic layer was washed with water and brine, dried over Na2 SO4 and evaporated to yield a colorless solid. cooled to −5° C. The reaction mixture was stirred for 3 h at rt was then quenched by addition of sat. aqueous NaHCO3 solution The organic layer was washed with water and brine dried over Na2 SO4 evaporated to yield a colorless solid

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 1-benzylpiperidine-4-carboxylic acid (1 g, 4.56 mmol), methylamine (9.12 ml of a 2N solution in THF, 18.2 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (1.75 g, 9.1 mmol) and 1-hydroxybenzotriazole (0.7 g, 4.56 mmol) in 10 ml DMF was stirred at rt for 3 h. The reaction mixture was poured on saturated aqueous NaHCO3 and extracted with ethyl acetate. The organic layer was washed with NaHCO3 solution and brine, dried (Na2 SO4) and evaporated. Drying in vacuo gave a colorless solid which was used in the next step without further purification. extracted with ethyl acetate The organic layer was washed with NaHCO3 solution and brine dried (Na2 SO4) evaporated Drying in vacuo gave a colorless solid which was used in the next step without further purification

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: N-Benzyl 4-piperidinecarboxylic acid (5.00 g, 22.8 mmol), 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (5.25 g, 27.4 mmol) and 1-hydroxybenzotriazole hydrate (3.84 g, 25.1 mmol) were added to a solution of methylamine (11.4 ml of a 2.0M solution in tetrahydrofuran, 22.8 mmol) in dichloromethane (100 ml). The mixture was stirred for 1 hour at room temperature, then partitioned between dichloromethane and water. The organic layer was separated and washed with brine, dried (MgSO4), filtered and evaporated under reduced pressure to furnish a pale yellow solid, 3.50 g. partitioned between dichloromethane and water The organic layer was separated washed with brine dried (MgSO4) filtered evaporated under reduced pressure to furnish a pale yellow solid, 3.50 g

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 1-benzyl-piperidine-4-carboxylic acid methylamide (36) (853 mg, 3.67 mmol) in dichloromethane (10 ml) was cooled in an ice-bath and phosphorous pentachloride (841 mg, 4 mmol) was added dropwise. The mixture was stirred at rt for 5 h, cooled to −5° C. and trimethylsilyl azide (387 ul, 3.67 mmol) was added dropwise. The reaction mixture was stirred for 3 h at rt and was then quenched by addition of sat. aqueous NaHCO3 solution. The organic layer was washed with water and brine, dried over Na2 SO4 and evaporated to yield a colorless solid. cooled to −5° C. The reaction mixture was stirred for 3 h at rt was then quenched by addition of sat. aqueous NaHCO3 solution The organic layer was washed with water and brine dried over Na2 SO4 evaporated to yield a colorless solid

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 1-benzylpiperidine-4-carboxylic acid (1 g, 4.56 mmol), methylamine (9.12 ml of a 2N solution in THF, 18.2 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (1.75 g, 9.1 mmol) and 1-hydroxybenzotriazole (0.7 g, 4.56 mmol) in 10 ml DMF was stirred at rt for 3 h. The reaction mixture was poured on saturated aqueous NaHCO3 and extracted with ethyl acetate. The organic layer was washed with NaHCO3 solution and brine, dried (Na2 SO4) and evaporated. Drying in vacuo gave a colorless solid which was used in the next step without further purification. extracted with ethyl acetate The organic layer was washed with NaHCO3 solution and brine dried (Na2 SO4) evaporated Drying in vacuo gave a colorless solid which was used in the next step without further purification