1-prop-2-enylpiperidine

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: The piperidine from Example 114 (56 mg, 0.15 mmol) was dissolved in dimethylformamide (2 mL) and was treated with allyl bromide (17 μL, 0.18 mmol), and potassium carbonate (63 mg, 0.45 mmol) and the mixture was stirred at r.t. for 4 hrs. The mixture was diluted with water (2 mL) and the solution was washed with ethyl acetate (3×10 mL). The organic phase was dried (MgSO4) and evaporated to give a pale oil which was purified by column chromatography on silica gel eluting with 80% ethyl acetate in hexanes to give the N-allylpiperidin. 1H NMR (CDCl3) 7.42-7.37 (4H, m), 7.13-7.02 (2H, m), 6.90-6.83 (1H, m), 5.83-5.71 (1H, m), 5.12-5.08 (2H, m), 2.99-2.95 (2H, m), 2.86 (2H, d, J=6.5 Hz), 2.84-2.38 (4H, m), and 1.91-1.85 (2H, m); MS MH+=412(414). the solution was washed with ethyl acetate (3×10 mL) The organic phase was dried (MgSO4) evaporated to give a pale oil which was purified by column chromatography on silica gel eluting with 80% ethyl acetate in hexanes

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 213 9 of piperidine dissolved in 300 mL of diethyl ether and was added to a 1 L 3-necked round-bottomed flask. The mixture was cooled to 5° C. with an ice bath. While stirring, a solution of 151.2 g of allyl bromide in 60 mL of diethyl ether was added slowly to the piperidine solution. After addition was complete, the reaction mixture was allowed to stir at room temperature for 18 hours. The white precipitate formed was removed by filtration. Ether was removed from the filtrate at room temperature using a rotary evaporator. The residual liquid was fractionally distilled yielding 108 g of N-allylpiperidine. To a 500 mL 3-necked round-bottomed flask was added 40.1 9 of N-allylpiperidine dissolved in 50 mL of diethyl either. After cooling to 5° C. with an ice bath, a solution of 38.7 g of allyl bromide in 30 mL of diethyl ether was added slowly. After completion of addition of allyl bromide the reaction mixture was allowed to warm to room temperature and stirred at room temperature for 24 hours. The solid residue thus formed was collected by filtration and was washed twice with 1.5 L of diethyl ether. The washed solid was dried under vacuum yielding 44 9 of N,N-diallylpiperidinium bromide as a white solid. dissolved in 50 mL of diethyl either to warm to room temperature The solid residue thus formed was collected by filtration was washed twice with 1.5 L of diethyl ether The washed solid was dried under vacuum

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 213 9 of piperidine dissolved in 300 mL of diethyl ether and was added to a 1 L 3-necked round-bottomed flask. The mixture was cooled to 5° C. with an ice bath. While stirring, a solution of 151.2 g of allyl bromide in 60 mL of diethyl ether was added slowly to the piperidine solution. After addition was complete, the reaction mixture was allowed to stir at room temperature for 18 hours. The white precipitate formed was removed by filtration. Ether was removed from the filtrate at room temperature using a rotary evaporator. The residual liquid was fractionally distilled yielding 108 g of N-allylpiperidine. To a 500 mL 3-necked round-bottomed flask was added 40.1 9 of N-allylpiperidine dissolved in 50 mL of diethyl either. After cooling to 5° C. with an ice bath, a solution of 38.7 g of allyl bromide in 30 mL of diethyl ether was added slowly. After completion of addition of allyl bromide the reaction mixture was allowed to warm to room temperature and stirred at room temperature for 24 hours. The solid residue thus formed was collected by filtration and was washed twice with 1.5 L of diethyl ether. The washed solid was dried under vacuum yielding 44 9 of N,N-diallylpiperidinium bromide as a white solid. was added to a 1 L 3-necked round-bottomed flask After addition to stir at room temperature for 18 hours The white precipitate formed was removed by filtration Ether was removed from the filtrate at room temperature a rotary evaporator The residual liquid was fractionally distilled

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 213 9 of piperidine dissolved in 300 mL of diethyl ether and was added to a 1 L 3-necked round-bottomed flask. The mixture was cooled to 5° C. with an ice bath. While stirring, a solution of 151.2 g of allyl bromide in 60 mL of diethyl ether was added slowly to the piperidine solution. After addition was complete, the reaction mixture was allowed to stir at room temperature for 18 hours. The white precipitate formed was removed by filtration. Ether was removed from the filtrate at room temperature using a rotary evaporator. The residual liquid was fractionally distilled yielding 108 g of N-allylpiperidine. To a 500 mL 3-necked round-bottomed flask was added 40.1 9 of N-allylpiperidine dissolved in 50 mL of diethyl either. After cooling to 5° C. with an ice bath, a solution of 38.7 g of allyl bromide in 30 mL of diethyl ether was added slowly. After completion of addition of allyl bromide the reaction mixture was allowed to warm to room temperature and stirred at room temperature for 24 hours. The solid residue thus formed was collected by filtration and was washed twice with 1.5 L of diethyl ether. The washed solid was dried under vacuum yielding 44 9 of N,N-diallylpiperidinium bromide as a white solid. was added to a 1 L 3-necked round-bottomed flask After addition to stir at room temperature for 18 hours The white precipitate formed was removed by filtration Ether was removed from the filtrate at room temperature a rotary evaporator The residual liquid was fractionally distilled

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: The piperidine from Example 114 (56 mg, 0.15 mmol) was dissolved in dimethylformamide (2 mL) and was treated with allyl bromide (17 μL, 0.18 mmol), and potassium carbonate (63 mg, 0.45 mmol) and the mixture was stirred at r.t. for 4 hrs. The mixture was diluted with water (2 mL) and the solution washed with ethyl acetate (3×10 mL). The organic phase was dried (MgSO4) and evaporated to give a pale oil which was purified by column chromatography on silica gel eluting with 80% ethyl acetate in hexanes to give the N-allylpiperidine. 1H NMR (CDCl3) 7.42-7.37 (4H, m), 7.13-7.02 (2H, m), 6.90-6.83 (1H, m), 5.83-5.71 (1H, m), 5.12-5.08 (2H, m), 2.99-2.95 (2H, m), 2.86 (2H, d, J=6.5 Hz), 2.84-2.38 (4H, m), and 1.91-1.85 (2H, m); MS MH+=412(414). the solution washed with ethyl acetate (3×10 mL) The organic phase was dried (MgSO4) evaporated to give a pale oil which was purified by column chromatography on silica gel eluting with 80% ethyl acetate in hexanes

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-[(6-trifluoromethanesulfonyloxy-1,2,3,4-tetrahydro-naphthalen-1-ylcarbamoyl)-methyl]-piperidine-1-carboxylic acid tert-butyl ester (624 mg, 1.19 mmol) in CH3CN (6 mL) was purged with N2, and then added palladium(II)acetate (Strem Chemicals, 20 mg, 0.09 mmol), 1,1′-bis(diphenylphosphino)ferrocene (Aldrich, 211 mg, 0.38 mmol), K2CO3 (Aldrich, 299 mg, 2.16 mmol) and 1-allylpiperidine (Lancaster, 904 mg, 7.22 mmol). The mixture was heated to 80° C. overnight, cooled to RT, diluted with water (10 mL), and extracted with ether. The organic solution was dried over Na2SO4, filtered and concentrated in vacuo. The crude was purified by silica gel chromatography (26% EtOAc-Hexane) to provide the title compound. MS (ESI): 496 (M+H)+. cooled to RT extracted with ether The organic solution was dried over Na2SO4 filtered concentrated in vacuo The crude was purified by silica gel chromatography (26% EtOAc-Hexane)

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

Procedure: The piperidine from Example 114 (56 mg, 0.15 mmol) was dissolved in dimethylformamide (2 mL) and was treated with allyl bromide (17 μL, 0.18 mmol), and potassium carbonate (63 mg, 0.45 mmol) and the mixture was stirred at r.t. for 4 hrs. The mixture was diluted with water (2 mL) and the solution was washed with ethyl acetate (3×10 mL). The organic phase was dried (MgSO4) and evaporated to give a pale oil which was purified by column chromatography on silica gel eluting with 80% ethyl acetate in hexanes to give the N-allylpiperidin. 1H NMR (CDCl3) 7.42-7.37 (4H, m), 7.13-7.02 (2H, m), 6.90-6.83 (1H, m), 5.83-5.71 (1H, m), 5.12-5.08 (2H, m), 2.99-2.95 (2H, m), 2.86 (2H, d, J=6.5 Hz), 2.84-2.38 (4H, m), and 1.91-1.85 (2H, m); MS MH+=412(414). the solution was washed with ethyl acetate (3×10 mL) The organic phase was dried (MgSO4) evaporated to give a pale oil which was purified by column chromatography on silica gel eluting with 80% ethyl acetate in hexanes