1-prop-2-enylpiperidin-4-ol

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

Procedure: To a 500 mL 3-necked round-bottomed flask, was added 24.0 g of 4-hydroxypiperidine dissolved in 140 mL of acetone. To this mixture was added 40.9 g of powdered anhydrous potassium carbonate. The reaction mixture was cooled to 5° C. with an ice bath. While stirring, 28.7 9 of allyl bromide in 60 mL acetone was added slowly to the reaction mixture. After addition was complete, the reaction mixture was allowed to stir at room temperature for 18 hours. The solid residue was removed by filtration, and acetone was removed from the filtrate using a rotary evaporator yielding 25.0 g of N-allyl(4-hydroxy)piperidine as viscous liquid. To a 500 mL 3-necked round-bottomed flask was added 20 g of N-allyl(4-hydroxy)piperidine dissolved in 75 mL diethyl ether. After cooling to 5° C. with an ice bath, 21.4 g of allyl bromide dissolved 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 with diethyl ether (2×1.5 L). The washed solid was recrystallized from acetonitrile. After removal of acetonitrile by filtration, the residue was dried under vacuum yielding 22 9 of N,N-diallyl(4-hydroxy)piperidinium bromide as a white solid. was added slowly to warm to room temperature The solid residue thus formed was collected by filtration was washed with diethyl ether (2×1.5 L) The washed solid was recrystallized from acetonitrile After removal of acetonitrile by filtration the residue was dried under vacuum

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

Procedure: To a 500 mL 3-necked round-bottomed flask, was added 24.0 g of 4-hydroxypiperidine dissolved in 140 mL of acetone. To this mixture was added 40.9 g of powdered anhydrous potassium carbonate. The reaction mixture was cooled to 5° C. with an ice bath. While stirring, 28.7 9 of allyl bromide in 60 mL acetone was added slowly to the reaction mixture. After addition was complete, the reaction mixture was allowed to stir at room temperature for 18 hours. The solid residue was removed by filtration, and acetone was removed from the filtrate using a rotary evaporator yielding 25.0 g of N-allyl(4-hydroxy)piperidine as viscous liquid. To a 500 mL 3-necked round-bottomed flask was added 20 g of N-allyl(4-hydroxy)piperidine dissolved in 75 mL diethyl ether. After cooling to 5° C. with an ice bath, 21.4 g of allyl bromide dissolved 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 with diethyl ether (2×1.5 L). The washed solid was recrystallized from acetonitrile. After removal of acetonitrile by filtration, the residue was dried under vacuum yielding 22 9 of N,N-diallyl(4-hydroxy)piperidinium bromide as a white solid. After addition to stir at room temperature for 18 hours The solid residue was removed by filtration, and acetone was removed from the filtrate a rotary evaporator

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

Procedure: To a 500 mL 3-necked round-bottomed flask, was added 24.0 g of 4-hydroxypiperidine dissolved in 140 mL of acetone. To this mixture was added 40.9 g of powdered anhydrous potassium carbonate. The reaction mixture was cooled to 5° C. with an ice bath. While stirring, 28.7 9 of allyl bromide in 60 mL acetone was added slowly to the reaction mixture. After addition was complete, the reaction mixture was allowed to stir at room temperature for 18 hours. The solid residue was removed by filtration, and acetone was removed from the filtrate using a rotary evaporator yielding 25.0 g of N-allyl(4-hydroxy)piperidine as viscous liquid. To a 500 mL 3-necked round-bottomed flask was added 20 g of N-allyl(4-hydroxy)piperidine dissolved in 75 mL diethyl ether. After cooling to 5° C. with an ice bath, 21.4 g of allyl bromide dissolved 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 with diethyl ether (2×1.5 L). The washed solid was recrystallized from acetonitrile. After removal of acetonitrile by filtration, the residue was dried under vacuum yielding 22 9 of N,N-diallyl(4-hydroxy)piperidinium bromide as a white solid. After addition to stir at room temperature for 18 hours The solid residue was removed by filtration, and acetone was removed from the filtrate a rotary evaporator

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

Procedure: Into a mixture of 4-hydroxypiperidine (75 g, 0.74 mol) and potassium carbonate (104 g, 0.75 mol) in ethanol (250 ml) is added allyl bromide (65 ml, 0.74 mol) in four equal portions over a three-hour period. After the addition is complete, the reaction mixture is stirred at ambient temperature until the disappearance of the reactants, as determined by TLC analysis (approximately six hours). The insoluble solids formed are then removed by filtration and the filtrate is concentrated in vacuo. The residue is purified by flash chromatography on silica gel with a mixture of 25% (vol.) methanol in ethyl acetate as the solvent to give 53.2 g (51% yield) of the title compound as a yellow oil. After the addition as determined by TLC analysis (approximately six hours) The insoluble solids formed are then removed by filtration the filtrate is concentrated in vacuo The residue is purified by flash chromatography on silica gel with a mixture of 25% (vol.) methanol in ethyl acetate as the solvent

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

Procedure: To a 500 mL 3-necked round-bottomed flask, was added 24.0 g of 4-hydroxypiperidine dissolved in 140 mL of acetone. To this mixture was added 40.9 g of powdered anhydrous potassium carbonate. The reaction mixture was cooled to 5° C. with an ice bath. While stirring, 28.7 9 of allyl bromide in 60 mL acetone was added slowly to the reaction mixture. After addition was complete, the reaction mixture was allowed to stir at room temperature for 18 hours. The solid residue was removed by filtration, and acetone was removed from the filtrate using a rotary evaporator yielding 25.0 g of N-allyl(4-hydroxy)piperidine as viscous liquid. To a 500 mL 3-necked round-bottomed flask was added 20 g of N-allyl(4-hydroxy)piperidine dissolved in 75 mL diethyl ether. After cooling to 5° C. with an ice bath, 21.4 g of allyl bromide dissolved 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 with diethyl ether (2×1.5 L). The washed solid was recrystallized from acetonitrile. After removal of acetonitrile by filtration, the residue was dried under vacuum yielding 22 9 of N,N-diallyl(4-hydroxy)piperidinium bromide as a white solid. was added slowly to warm to room temperature The solid residue thus formed was collected by filtration was washed with diethyl ether (2×1.5 L) The washed solid was recrystallized from acetonitrile After removal of acetonitrile by filtration the residue was dried under vacuum

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

Procedure: To a 500 mL 3-necked round-bottomed flask, was added 24.0 g of 4-hydroxypiperidine dissolved in 140 mL of acetone. To this mixture was added 40.9 g of powdered anhydrous potassium carbonate. The reaction mixture was cooled to 5° C. with an ice bath. While stirring, 28.7 9 of allyl bromide in 60 mL acetone was added slowly to the reaction mixture. After addition was complete, the reaction mixture was allowed to stir at room temperature for 18 hours. The solid residue was removed by filtration, and acetone was removed from the filtrate using a rotary evaporator yielding 25.0 g of N-allyl(4-hydroxy)piperidine as viscous liquid. To a 500 mL 3-necked round-bottomed flask was added 20 g of N-allyl(4-hydroxy)piperidine dissolved in 75 mL diethyl ether. After cooling to 5° C. with an ice bath, 21.4 g of allyl bromide dissolved 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 with diethyl ether (2×1.5 L). The washed solid was recrystallized from acetonitrile. After removal of acetonitrile by filtration, the residue was dried under vacuum yielding 22 9 of N,N-diallyl(4-hydroxy)piperidinium bromide as a white solid. After addition to stir at room temperature for 18 hours The solid residue was removed by filtration, and acetone was removed from the filtrate a rotary evaporator