3-(azepan-1-yl)propan-1-amine

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

Procedure: To a solution of 1-((2-(4-chlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid (0.25 g, 0.75 mmole), 3-(Azepan-1-yl)propan-1-amine (0.33 g) and DIPEA (0.32 mL) in DMF (5 mL) was added EDC (0.153 g). The reaction solution was stirred at room temperature overnight. The solvent removed and EtOAc (100 mL) was added. The organic layer was washed with saturated sodium bicarbonate (50 mL), water (50 mL) and dried over anhydrous magnesium sulfate. After filtration, the residue after concentration of the filtrate was crystallized from EtOAc/Hexane to provide the N-(3-(azepan-1-yl)propyl)-1-((2-(4-chlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxamide as white solid (0.30 g, 85%). H1NMR (300 MHz, CDCl3), ppm: 7.94 (d, 2H), 7.49 (m, 1H), 7.39 (d, 2H), 3.44 (s, 2H), 3.36 (m, 2H), 2.99 (d, 2H), 2.67 (m, 4H), 2.60 (t, 2H), 2.39 (s, 3H), 2.07 (m, 3H), 1.83 (m, 4H), 1.65 (m, 10H). MS (ESI+) M/z: 473, 475 (M+H). The solvent removed EtOAc (100 mL) was added The organic layer was washed with saturated sodium bicarbonate (50 mL), water (50 mL) dried over anhydrous magnesium sulfate After filtration the residue after concentration of the filtrate was crystallized from EtOAc/Hexane

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

Procedure: To a solution of 2-(3-(azepan-1-yl)propyl)isoindoline-1,3-dione (3.5 g) in Ethanol (20 mL) was added hydrazine (0.58 mL). The reaction mixture was reflux for 13 h and then cooled down to room temperature. TFA (2.0 mL) was added, the resulted white solid was filtered and the solvent was evaporated to give 3-(azepan-1-yl)propan-1-amine, used without further purification. The reaction mixture was reflux for 13 h the resulted white solid was filtered the solvent was evaporated

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

Procedure: To a solution of 2-(3-(azepan-1-yl)propyl)isoindoline-1,3-dione (3.5 g) in Ethanol (20 mL) was added hydrazine (0.58 mL). The reaction mixture was reflux for 13 h and then cooled down to room temperature. TFA (2.0 mL) was added, the resulted white solid was filtered and the solvent was evaporated to give 3-(azepan-1-yl)propan-1-amine, used without further purification. The reaction mixture was reflux for 13 h the resulted white solid was filtered the solvent was evaporated

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

Procedure: To a mixture of 3-(Azepan-1-yl)propan-1-amine (0.10 g, 0.64 mmole) in methylene chloride (5 mL) were added benzaldehyde (0.64 mmole) and NaBH(OAc)3 (0.63 g, 3.0 mmol). The reaction solution was stirred at room temperature for 3 h. Then, paraformaldehyde (200 mg) was added to the reaction mixture and stirring was continued for 6 h. 2N aqueous NaOH (2 mL) was added to quench the reaction, followed by addition of methylene chloride (30 mL). The organic layer was separated, dried over anhydrous Na2SO4, and filtered. The filtrate was evaporated to supply 3-(azepan-1-yl)-N-benzyl-N-methylpropan-1-amine (151 mg). stirring was continued for 6 h to quench the reaction The organic layer was separated dried over anhydrous Na2SO4 filtered The filtrate was evaporated to supply 3-(azepan-1-yl)-N-benzyl-N-methylpropan-1-amine (151 mg)

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

Procedure: To a mixture of 3-(Azepan-1-yl)propan-1-amine (0.10 g, 0.64 mmole) in methylene chloride (5 mL) were added benzaldehyde (0.64 mmole) and NaBH(OAc)3 (0.63 g, 3.0 mmol). The reaction solution was stirred at room temperature for 3 h. Then, paraformaldehyde (200 mg) was added to the reaction mixture and stirring was continued for 6 h. 2N aqueous NaOH (2 mL) was added to quench the reaction, followed by addition of methylene chloride (30 mL). The organic layer was separated, dried over anhydrous Na2SO4, and filtered. The filtrate was evaporated to supply 3-(azepan-1-yl)-N-benzyl-N-methylpropan-1-amine (151 mg). stirring was continued for 6 h to quench the reaction The organic layer was separated dried over anhydrous Na2SO4 filtered The filtrate was evaporated to supply 3-(azepan-1-yl)-N-benzyl-N-methylpropan-1-amine (151 mg)

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

Procedure: To a solution of 1-((2-(4-chlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid (0.25 g, 0.75 mmole), 3-(Azepan-1-yl)propan-1-amine (0.33 g) and DIPEA (0.32 mL) in DMF (5 mL) was added EDC (0.153 g). The reaction solution was stirred at room temperature overnight. The solvent removed and EtOAc (100 mL) was added. The organic layer was washed with saturated sodium bicarbonate (50 mL), water (50 mL) and dried over anhydrous magnesium sulfate. After filtration, the residue after concentration of the filtrate was crystallized from EtOAc/Hexane to provide the N-(3-(azepan-1-yl)propyl)-1-((2-(4-chlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxamide as white solid (0.30 g, 85%). H1NMR (300 MHz, CDCl3), ppm: 7.94 (d, 2H), 7.49 (m, 1H), 7.39 (d, 2H), 3.44 (s, 2H), 3.36 (m, 2H), 2.99 (d, 2H), 2.67 (m, 4H), 2.60 (t, 2H), 2.39 (s, 3H), 2.07 (m, 3H), 1.83 (m, 4H), 1.65 (m, 10H). MS (ESI+) M/z: 473, 475 (M+H). The solvent removed EtOAc (100 mL) was added The organic layer was washed with saturated sodium bicarbonate (50 mL), water (50 mL) dried over anhydrous magnesium sulfate After filtration the residue after concentration of the filtrate was crystallized from EtOAc/Hexane

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

Procedure: To a solution of 2-(3-(azepan-1-yl)propyl)isoindoline-1,3-dione (3.5 g) in Ethanol (20 mL) was added hydrazine (0.58 mL). The reaction mixture was reflux for 13 h and then cooled down to room temperature. TFA (2.0 mL) was added, the resulted white solid was filtered and the solvent was evaporated to give 3-(azepan-1-yl)propan-1-amine, used without further purification. The reaction mixture was reflux for 13 h the resulted white solid was filtered the solvent was evaporated

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

Procedure: To a mixture of 3-(Azepan-1-yl)propan-1-amine (0.10 g, 0.64 mmole) in methylene chloride (5 mL) were added benzaldehyde (0.64 mmole) and NaBH(OAc)3 (0.63 g, 3.0 mmol). The reaction solution was stirred at room temperature for 3 h. Then, paraformaldehyde (200 mg) was added to the reaction mixture and stirring was continued for 6 h. 2N aqueous NaOH (2 mL) was added to quench the reaction, followed by addition of methylene chloride (30 mL). The organic layer was separated, dried over anhydrous Na2SO4, and filtered. The filtrate was evaporated to supply 3-(azepan-1-yl)-N-benzyl-N-methylpropan-1-amine (151 mg). stirring was continued for 6 h to quench the reaction The organic layer was separated dried over anhydrous Na2SO4 filtered The filtrate was evaporated to supply 3-(azepan-1-yl)-N-benzyl-N-methylpropan-1-amine (151 mg)