2-piperidin-4-ylethanamine

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

Procedure: In a similar manner to Example 31, a mixture of 4-(2-aminoethyl)piperidine (5.0 g), 4'-chloroacetophenone (6.04 g), p-toluenesulphonic acid (catalytic amount) and toluene (100 ml) was boiled under reflux for 10 hours with water removal using a Dean and Stark apparatus. The mixture was cooled to ambient temperature and 2-bromoethyl phenyl ether (7.85 g) and triethylamine (5.4 ml) added. The mixture was boiled under reflux for 6 hours. The solvent was evaporated off and the residue dissolved in ethanol (100 ml) and sodium borohydride (3.4 g) was added. The mixture was boiled under reflux for 4 hours then worked up to give an oil which was purified by flash column chromatography on silica using ethyl acetate/triethylamine (95:5) as the mobile phase to give 4-{2-[1-(4-chlorophenyl)ethylamino]ethyl}-1-(2-phenoxyethyl)piperidine as an oil. under reflux for 6 hours The solvent was evaporated off the residue dissolved in ethanol (100 ml) sodium borohydride (3.4 g) was added under reflux for 4 hours to give an oil which was purified by flash column chromatography on silica

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

Procedure: As an alternative to obtaining a mixture of Schiff bases VI and VI(a) or VI(b), the reaction can be conducted stepwise. For example, 4-(2-aminoethyl)piperidine may be converted to a Schiff base with 1,5-di-[3,3-dimethylbicyclo[2.2.1]hept-2-yl]pentan-3-one, catalytically reduced, the ring nitrogen selectively cyanoethylated with acrylonitrile, followed by catalytic hydrogenation to furnish 1-(3-aminopropyl)-4-[2-(1,5-di-[3,3-dimethylbicyclo[2.2.1]hept-2-yl]-3-pentylamino)ethyl]piperidine. As an alternative to obtaining the reaction

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

Procedure: In a similar manner to Example 31, a mixture of 4-(2-aminoethyl)piperidine (5.0 g), 4'-chloroacetophenone (6.04 g), p-toluenesulphonic acid (catalytic amount) and toluene (100 ml) was boiled under reflux for 10 hours with water removal using a Dean and Stark apparatus. The mixture was cooled to ambient temperature and 2-bromoethyl phenyl ether (7.85 g) and triethylamine (5.4 ml) added. The mixture was boiled under reflux for 6 hours. The solvent was evaporated off and the residue dissolved in ethanol (100 ml) and sodium borohydride (3.4 g) was added. The mixture was boiled under reflux for 4 hours then worked up to give an oil which was purified by flash column chromatography on silica using ethyl acetate/triethylamine (95:5) as the mobile phase to give 4-{2-[1-(4-chlorophenyl)ethylamino]ethyl}-1-(2-phenoxyethyl)piperidine as an oil. under reflux for 6 hours The solvent was evaporated off the residue dissolved in ethanol (100 ml) sodium borohydride (3.4 g) was added under reflux for 4 hours to give an oil which was purified by flash column chromatography on silica