(1-benzylpiperidin-4-yl)methanamine

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: A mixture of 1-(phenylmethyl)-4-piperidinemethanamine (0.076 mol) and acrylonitrile (0.076 mol) in ethanol (250 ml) was stirred and refluxed for 4 hours. The solvent was evaporated, yielding 20.0 g (102.4%, crude residue, used in next reaction step, without further purification) of 3-[[[1-(phenylmethyl)-4-piperidinyl]methyl]amino]-propanenitrile (interm. 14). refluxed for 4 hours The solvent was evaporated

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

Procedure: A mixture of 1-(phenylmethyl)-4-piperidinemethanamine (0.076 mol) and acrylo-nitrile (0.076 mol) in ethanol (250 ml) was stirred and refluxed for 4 hours. The solvent was evaporated, yielding 20.0 g (102.4%, crude residue, used in next reaction step, without further purification) of 3-[[[1-(phenylmethyl)-4-piperidinyl]methyl]-amino]-propanenitrile (interm. 14). refluxed for 4 hours The solvent was evaporated

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

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

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2.2 g of 1-benzylisonipecotamide in 50 ml of tetrahydrofuran was added 1.58 g of lithium aluminum hydride at 0° C. and the resulting mixture was heated under reflux for 2 hours. Then the reaction mixture was cooled to 0° C. After adding water and a 10% aqueous solution of sodium hydroxide, the insoluble matters were filtered off. After distilling off the solvent under reduced pressure, 2.0 g of the title compound was obtained as a brown oily substance. the resulting mixture was heated under reflux for 2 hours a 10% aqueous solution of sodium hydroxide, the insoluble matters were filtered off After distilling off the solvent under reduced pressure

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

Procedure: Indole-3-carboxylic acid was converted to its acid chloride and then reacted with (1-benzyl-4-piperidyl)methylamine (D10) as in the method of Description 1b to afford N-[(1-benzyl-4-piperidyl)methyl] indole-3-carboxamide as a white solid (60%).

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

Procedure: A mixture of 1-(phenylmethyl)-4-piperidinemethanamine (0.076 mol) and acrylonitrile (0.076 mol) in ethanol (250 ml) was stirred and refluxed for 4 hours. The solvent was evaporated, yielding 20.0 g (102.4%, crude residue, used in next reaction step, without further purification) of 3-[[[1-(phenylmethyl)-4-piperidinyl]methyl]amino]-propanenitrile (interm. 14). refluxed for 4 hours The solvent was evaporated

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

Procedure: A mixture of 1-(phenylmethyl)-4-piperidinemethanamine (0.076 mol) and acrylo-nitrile (0.076 mol) in ethanol (250 ml) was stirred and refluxed for 4 hours. The solvent was evaporated, yielding 20.0 g (102.4%, crude residue, used in next reaction step, without further purification) of 3-[[[1-(phenylmethyl)-4-piperidinyl]methyl]-amino]-propanenitrile (interm. 14). refluxed for 4 hours The solvent was evaporated

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

Procedure: A mixture of 1-(phenylmethyl)-4-piperidinemethanamine (0.076 mol) and acrylo-nitrile (0.076 mol) in ethanol (250 ml) was stirred and refluxed for 4 hours. The solvent was evaporated, yielding 20.0 g (102.4%, crude residue, used in next reaction step, without further purification) of 3-[[[1-(phenylmethyl)-4-piperidinyl]methyl]-amino]-propanenitrile (interm. 14). refluxed for 4 hours The solvent was evaporated

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

Procedure: A solution of 1-benzyl-4-carbamoylpiperidine (2.5 g) in tetrahydrofuran (10 ml) was added dropwise to 1N solution of diborane-tetrahydrofuran complex in tetrahydrofuran (34.3 ml) at 0° C. and then the mixture was refluxed for 3 hours. After cooling to room temperature, 6N hydrochloric acid (10 ml) was added thereto. The mixture was stirred overnight and concentrated in vacuo. The residue was dissolved in ethyl acetate and made basic with 5N sodium hydroxide. The separated organic layer was washed with water and brine and dried over magnesium sulfate, and evaporated in vacuo to give (1-benzylpiperidin-4-yl)methylamine (1.4 g) as an oil. the mixture was refluxed for 3 hours concentrated in vacuo The residue was dissolved in ethyl acetate The separated organic layer was washed with water and brine dried over magnesium sulfate evaporated in vacuo