6-(4-phenylbutoxy)hexan-1-amine

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

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

Procedure: A solution of 46.6 g (0.15 mol) of 6-(4-phenylbutoxy)-hexyl-bromide and 27.6 g (0.15 mol) of potassium phthalimide in 400 ml of acetone is refluxed for 70 hours. After cooling, the potassium bromide precipitated is removed by suction filtering and the solvent is distilled off in vacuo. The oily residue thus obtained, consisting of crude 6-(4-phenyl-butoxy)-N-hexyl-phthalimide, is stirred into 300 ml of dichloromethane and 300 ml of 40% methylamine solution overnight. The organic phase is separated off and the aqueous phase is extracted twice more with dichloromethane. The combined organic phases are dried over sodium sulphate and evaporated down in vacuo. The oily residue is dissolved in ether, the solids precipitated are filtered off and the filtrate is evaporated to dryness. The colorless oil remaining is distilled. Bp0.2 =143°-145° C. After cooling the potassium bromide precipitated is removed by suction filtering the solvent is distilled off in vacuo The oily residue thus obtained The organic phase is separated off the aqueous phase is extracted twice more with dichloromethane The combined organic phases are dried over sodium sulphate evaporated down in vacuo The oily residue is dissolved in ether the solids precipitated are filtered off the filtrate is evaporated to dryness The colorless oil remaining is distilled Bp0.2 =143°-145° C.

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

Procedure: A solution of 46.6 g (0.15 mol) of 6-(4-phenylbutoxy)-hexyl-bromide and 27.6 g (0.15 mol) of potassium phthalimide in 400 ml of acetone is refluxed for 70 hours. After cooling, the potassium bromide precipitated is removed by suction filtering and the solvent is distilled off in vacuo. The oily residue thus obtained, consisting of crude 6-(4-phenyl-butoxy)-N-hexyl-phthalimide, is stirred into 300 ml of dichloromethane and 300 ml of 40% methylamine solution overnight. The organic phase is separated off and the aqueous phase is extracted twice more with dichloromethane. The combined organic phases are dried over sodium sulphate and evaporated down in vacuo. The oily residue is dissolved in ether, the solids precipitated are filtered off and the filtrate is evaporated to dryness. The colorless oil remaining is distilled. Bp0.2 =143°-145° C. After cooling the potassium bromide precipitated is removed by suction filtering the solvent is distilled off in vacuo The oily residue thus obtained The organic phase is separated off the aqueous phase is extracted twice more with dichloromethane The combined organic phases are dried over sodium sulphate evaporated down in vacuo The oily residue is dissolved in ether the solids precipitated are filtered off the filtrate is evaporated to dryness The colorless oil remaining is distilled Bp0.2 =143°-145° C.

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

Procedure: A solution of 46.6 g (0.15 mol) of 6-(4-phenylbutoxy)-hexyl-bromide and 27.6 g (0.15 mol) of potassium phthalimide in 400 ml of acetone is refluxed for 70 hours. After cooling, the potassium bromide precipitated is removed by suction filtering and the solvent is distilled off in vacuo. The oily residue thus obtained, consisting of crude 6-(4-phenyl-butoxy)-N-hexyl-phthalimide, is stirred into 300 ml of dichloromethane and 300 ml of 40% methylamine solution overnight. The organic phase is separated off and the aqueous phase is extracted twice more with dichloromethane. The combined organic phases are dried over sodium sulphate and evaporated down in vacuo. The oily residue is dissolved in ether, the solids precipitated are filtered off and the filtrate is evaporated to dryness. The colorless oil remaining is distilled. Bp0.2 =143°-145° C. After cooling the potassium bromide precipitated is removed by suction filtering the solvent is distilled off in vacuo The oily residue thus obtained The organic phase is separated off the aqueous phase is extracted twice more with dichloromethane The combined organic phases are dried over sodium sulphate evaporated down in vacuo The oily residue is dissolved in ether the solids precipitated are filtered off the filtrate is evaporated to dryness The colorless oil remaining is distilled Bp0.2 =143°-145° C.

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

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

Procedure: To a solution of 2.77 g (11.12 mmol) 6-(4-phenylbutoxy)hexylamine in 20 ml DMF is added 1.54 g (11.16 mmol) K2CO3 and 1.68 g (11.17 mmol) bromoacetaldehyde diethylacetal. After allowing the mixture to stand for 20 hr at 80° C., DMF is distilled off at reduced pressure, and the resulting crude product in 30 ml CH2Cl2 is washed with 30 ml H2O. The CH2Cl2 phase is dried on anhydrous Na2SO4, concentrated to dryness and the residue is purified by column chromatography on silica gel (gradient CH2Cl2/AcOEt 1:1 to AcOEt), thereby yielding 1.73 g (42.6 %) N-diethoxyethyl-6-(4-phenylbutoxy)hexylamine as an oil. DMF is distilled off at reduced pressure the resulting crude product in 30 ml CH2Cl2 is washed with 30 ml H2O The CH2Cl2 phase is dried on anhydrous Na2SO4 concentrated to dryness the residue is purified by column chromatography on silica gel (gradient CH2Cl2/AcOEt 1:1 to AcOEt)

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

Procedure: A solution of 4.02 g (11.86 mmol) N-benzyl-6-(4-phenylbutoxy)hexylamine in 40 ml EtOH is hydrogenated at room temperature and atmospheric pressure with 0.4 g 5% Pd/C. When 300 ml H2 have been absorbed, the mixture is filtered on decalite and the filtrate is concentrated to yield 2.89 g (97.9%) 6-(4-phenylbutoxy)hexylamine as an oil. is hydrogenated at room temperature When 300 ml H2 have been absorbed the mixture is filtered on decalite the filtrate is concentrated

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

Procedure: A solution of 46.6 g (0.15 mol) of 6-(4-phenylbutoxy)-hexyl-bromide and 27.6 g (0.15 mol) of potassium phthalimide in 400 ml of acetone is refluxed for 70 hours. After cooling, the potassium bromide precipitated is removed by suction filtering and the solvent is distilled off in vacuo. The oily residue thus obtained, consisting of crude 6-(4-phenyl-butoxy)-N-hexyl-phthalimide, is stirred into 300 ml of dichloromethane and 300 ml of 40% methylamine solution overnight. The organic phase is separated off and the aqueous phase is extracted twice more with dichloromethane. The combined organic phases are dried over sodium sulphate and evaporated down in vacuo. The oily residue is dissolved in ether, the solids precipitated are filtered off and the filtrate is evaporated to dryness. The colorless oil remaining is distilled. Bp0.2 =143°-145° C. After cooling the potassium bromide precipitated is removed by suction filtering the solvent is distilled off in vacuo The oily residue thus obtained The organic phase is separated off the aqueous phase is extracted twice more with dichloromethane The combined organic phases are dried over sodium sulphate evaporated down in vacuo The oily residue is dissolved in ether the solids precipitated are filtered off the filtrate is evaporated to dryness The colorless oil remaining is distilled Bp0.2 =143°-145° C.